Cefdinir

Identification

Summary

Cefdinir is a third generation cephalosporin used to treat susceptible Gram negative and Gram positive bacterial infections.

Generic Name

Cefdinir

DrugBank Accession Number

DB00535

Background

Cefdinir, also known as Omnicef, is a semi-synthetic, broad-spectrum antibiotic belonging to the third generation of the cephalosporin class. It has been proven to be effective for the treatment of common bacterial infections in the ear, sinus, throat, lungs, and skin. Cefdinir was approved by the FDA in 1997 to treat a variety of mild to moderate infections and was initially marketed by Abbvie.⁶ Because of its chemical structure, it is effective against organisms that are resistant to first-line cephalosporin therapy due to the production of beta-lactamase enzymes.^2,3

Type

Small Molecule

Groups

Approved

Structure

Similar Structures

Weight: Average: 395.414
Monoisotopic: 395.035809931
Chemical Formula: C₁₄H₁₃N₅O₅S₂

Synonyms

(6R,7R,Z)-7-(2-(2-aminothiazol-4-yl)-2-(hydroxyimino)acetamido)-8-oxo-3-vinyl-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid
(6R,7R)-7-{2-(2-Amino-thiazol-4-yl)-2-[(Z)-hydroxyimino]-acetylamino}-8-oxo-3-vinyl-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid
Cefdinir
Cefdinirum
CFDN

External IDs

BMY-28488
CI 983
CI-983
FK 482
FK-482

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Pharmacology

Indication

Cefdinir is indicated to treat acute bacterial otitis media, acute maxillary sinusitis, community-acquired (CA) pneumonia, acute bacterial exacerbations of chronic bronchitis, pharyngitis/tonsillitis, and uncomplicated skin and skin structure infections in children and adults.^14,6

The organisms susceptible to cefdinir have been listed below in addition to their associated clinical condition that may be treated with cefdinir.¹⁴ Various beta-lactamase producing organisms may be treated, as indicated in certain sections below.

Respiratory Acute bacterial exacerbations of chronic bronchitis caused by Haemophilus influenzae, Haemophilus parainfluenzae, Streptococcus pneumoniae (penicillin-susceptible only), and Moraxella catarrhalis

Community-acquired pneumonia caused by Haemophilus influenzae, Haemophilus parainfluenzae, Streptococcus pneumoniae (penicillin-susceptible only), and Moraxella catarrhalis

Ear, nose, and throat Acute bacterial otitis media caused by Haemophilus influenzae, Moraxella catarrhalis, and Streptococcus pneumoniae (penicillin-susceptible only)

Tonsillitis caused by Streptococcus pyogenes

Pharyngitis caused by Streptococcus pyogenes

Acute maxillary sinusitis caused by Haemophilus pneumoniae and Streptococcus pneumoniae (penicillin-susceptible only), and Moraxella catarrhalis

Skin and skin structure infections

Uncomplicated skin and skin structure infections caused by Staphylococcus aureus and Streptococcus pyogenes

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Associated Conditions

Indication Type	Indication	Combined Product Details	Approval Level	Age Group	Dose Form
Used in combination to treat	Acute exacerbation of chronic bronchitis (aecb)	Combination Product in combination with: Clavulanic acid (DB00766)	••••••••••••		••••••• ••••••• ••••••• ••••••• ••••••••••••
Treatment of	Acute exacerbation of chronic bronchitis caused by haemophilus influenza		••••••••••••	••••••••••• •••••	•••••••• ••••••••••
Treatment of	Acute exacerbation of chronic bronchitis caused by streptococcus pneumoniae		••••••••••••	••••••••••• •••••	•••••••• ••••••••••
Treatment of	Acute exacerbation of chronic bronchitis caused by haemophilus parainfluenzae		••••••••••••	••••••••••• •••••	•••••••• ••••••••••
Treatment of	Acute exacerbation of chronic bronchitis caused by moraxella catarrhalis		••••••••••••	••••••••••• •••••	•••••••• ••••••••••

Contraindications & Blackbox Warnings

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Pharmacodynamics

Cefdinir is a bactericidal agent that treats bacterial infections by interfering with cell wall synthesis.¹⁴ Cefdinir exerts broad-spectrum activity against a variety of gram-positive and gram-negative bacterial infections. It is effective against several beta-lactamase enzyme producing bacteria. As a result, many organisms that are resistant to other cephalosporins may be susceptible to cefdinir.^3,4,17

Mechanism of action

Five-member thiazolidine rings that make up penicillins are replaced in cephalosporins by a six-member dihydrothiazine ring, conferring greater bactericidal activity. This This 6-member ring enables cefdinir and other cephalosporins to resist inactivation by certain bacterial enzymes.¹²

With a mechanism similar to other beta-lactam antibiotics, the bactericidal activity of cefdinir is caused by the inhibition of cell wall synthesis via binding to penicillin-binding proteins (PBPs). Cefdinir, like other cephalosporins, penetrates the bacterial cell wall, combats inactivation by beta-lactamase enzymes, and inactivates penicillin-binding proteins.¹² This interferes with the final step of transpeptidation in cell walls, eventually leading to cell lysis, which eventually leads to the death of bacteria that are susceptible to this drug.² Cefdinir has shown affinity to penicillin protein binding proteins 2 and 3. ^7,8,9 It has also been shown to inhibit transpeptidase enzymes of various bacteria, which may play a role in its bactericidal action.^10,11 One in vitro study suggests that cefdinir inhibits myeloperoxidase release extracellularly.¹³ The impact of this potential drug target in relation to its mechanism of action is unknown.

Target	Actions	Organism
APenicillin-binding protein 2	inhibitor	Neisseria gonorrhoeae
APBP3	inhibitor	Haemophilus influenzae
NMyeloperoxidase	inhibitor	Humans
UPeptidoglycan transpeptidase	inhibitor

Absorption

Maximal plasma cefdinir concentration can be attained between 2-4 hours after an ingested dose.¹⁴ The bioavailability of cefdinir depends on the formulation used. The estimated bioavailability of cefdinir in the capsule form is approximately 16%-21%, depending on the dose. Absolute bioavailability after the administration of a suspension of cefdinir is 25%.². The Cmax of cefdinir is 1.60 μg/mL after a 300 mg dose with an AUC of 7.05. Cmax is 2.87 μg/mL after a 600 mg dose with an AUC of 11.¹⁴ A meal high in fat can reduce the absorption of cefdinir by up to 15%, however, this is not a cause for clinically significant changes, therefore cefdinir may be taken with or without food.¹⁴ When given with aluminum or magnesium-containing antacids or iron, cefdinir absorption may decrease. It is recommended to allow 2 hours between cefdinir administration and the administration of these agents.²

Volume of distribution

The average volume of distribution of cefdinir in adults is about 0.35 L/kg and 0.67 L/kg in children.^14,18 Another resource estimates the volume of distribution in adults at 1.56–2.09 L/kg.² Cefdinir is found to be distributed in various tissues at clinically effective concentrations. It may be found in the epithelial lining fluid, bronchial mucosa, tonsils, sinuses, skin blister fluid, as well as the middle ear fluid.² Third-generation cephalosporins such as cefdinir cross the blood-brain barrier and are found in high concentrations in the cerebrospinal fluid, unlike their first and second generation counterparts.¹² The wide tissue distribution of cefdinir allows it to treat a variety of infections throughout the body.

Protein binding

The plasma protein binding of cefdinir ranges from 60% to approximately 70%.^2,14

Metabolism

This drug is not significantly metabolized and its pharmacological actions are mainly attributed to the parent drug.^2,14

Route of elimination

This drug is mainly excreted by the kidneys. Dose adjustments may be required for patients with renal impairment or patients on dialysis.¹⁴ Approximately 18.4% of a 300 mg dose of cefdinir was found unchanged in the urine after a 300 mg dose was administered during a pharmacokinetic study of 21 individuals.¹⁸ A large proportion of the administered dose is excreted in the feces, although the majority is found in the urine.¹²

Half-life

The average plasma elimination half-life is about 1.7 hours in adults.¹⁴ In children and healthy infants, plasma elimination half-life ranges from 1.2–1.5 hours.²

Clearance

The renal clearance in healthy adults in a pharmacokinetic study was 2.0 (± 1.0) mL/min/kg and the clearance in patients with renal failure was lower, decreasing in proportion to the degree of renal impairment.¹⁸ Dose adjustment is required in patients with renal impairment.¹⁴

Adverse Effects

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Toxicity

LD50 information Oral LD50 of cefdinir in the rat is >2000 mg/kg.¹⁵

There are limited data regarding cefdinir overdose in the literature. In studies of rodents, one 5600-mg/kg dose administered orally did not lead to adverse effects. Signs of toxicity and overdose caused by other beta-lactam antibiotics included nausea, vomiting, diarrhea, abdominal pain, and seizures.¹⁶

Pathways

Not Available

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Interactions

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This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.

Drug	Interaction
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Abacavir	Cefdinir may decrease the excretion rate of Abacavir which could result in a higher serum level.
Abciximab	The therapeutic efficacy of Abciximab can be decreased when used in combination with Cefdinir.
Aceclofenac	Aceclofenac may decrease the excretion rate of Cefdinir which could result in a higher serum level.
Acemetacin	Acemetacin may decrease the excretion rate of Cefdinir which could result in a higher serum level.
Acenocoumarol	The risk or severity of bleeding can be increased when Cefdinir is combined with Acenocoumarol.

Food Interactions

Avoid multivalent ions. Do not take aluminum, magnesium, or iron containing products up to 2 hours before or after this medication.
Take with or without food. The absorption is unaffected by food.

Products

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Product Ingredients

Ingredient	UNII	CAS	InChI Key
Cefdinir monohydrate	6E7SN358SE	213978-34-8	QWUVJQSNISEEQI-KYIYMPJCSA-N

Product Images

International/Other Brands

Cednir (Abbott) / Cefdiel (Ranbaxy) / Cefzon (Astellas) / Duocef (Ranbaxy) / Efdinir (Incepta) / Idinir (Invision) / Kefnir (Glenmark) / Nirocef (Sel-J) / Oceph (Zuventus) / Omicef (Sel-J) / Omnicef R (Janssen) / Palacef (Renata) / Palcef (Renata) / Rtist (Lupin) / Samnir (Siam Bheasach) / Xi Fu Ni (Central Pharm) / Zefdinir (Zydus) / Zinir (FDC)

Brand Name Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
Omnicef	Powder, for suspension	250 mg/5mL	Oral	AbbVie Inc.	1997-12-04	2011-05-31
Omnicef	Powder, for suspension	125 mg/5mL	Oral	AbbVie Inc.	1997-12-04	2011-05-31
Omnicef	Powder, for suspension	250 mg/5mL	Oral	Physicians Total Care, Inc.	1997-12-04	2012-06-30
Omnicef	Capsule	300 mg/1	Oral	AbbVie Inc.	1997-12-04	2011-05-31

Generic Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
Cefdinir	Capsule	300 mg/1	Oral	North Star Rx Llc	2007-08-16	2014-09-30
Cefdinir	Powder, for suspension	125 mg/5mL	Oral	Direct_Rx	2019-09-17	Not applicable
Cefdinir	Powder, for suspension	125 mg/5mL	Oral	Rpk Pharmaceuticals, Inc.	2007-12-14	Not applicable
Cefdinir	Capsule	300 mg/1	Oral	Preferred Pharmaceuticals Inc.	2016-08-23	2019-07-12
Cefdinir	Powder, for suspension	250 mg/5mL	Oral	Nucare Pharmaceuticals,inc.	2007-05-08	Not applicable

Mixture Products

Name	Ingredients	Dosage	Route	Labeller	Marketing Start	Marketing End
CEFBIR PLUS 300/125 MG FILM KAPLI TABLET, 20 ADET	Cefdinir (300 mg) + Clavulanate potassium (125 mg)	Tablet, coated	Oral	TAKEDA İLAÇ SAĞLIK SAN. TİC. LTD. ŞTİ.	2015-02-24	2017-10-06
ELUCEF PLUS 125/62.5 MG EFERVESAN TABLET, 20 ADET	Cefdinir (125 mg) + Clavulanate potassium (62.5 mg)	Tablet, effervescent	Oral	NEUTEC İLAÇ SAN. TİC. A.Ş.	2010-11-26	Not applicable
ELUCEF PLUS 125/62.5 MG SAŞE, 20 ADET	Cefdinir (125 mg) + Clavulanic acid (62.5 mg)	Powder	Oral	NEUTEC İLAÇ SAN. TİC. A.Ş.	2011-03-30	Not applicable
ELUCEF PLUS 300/125 MG EFERVESAN TABLET, 20 ADET	Cefdinir (300 mg) + Clavulanate potassium (125 mg)	Tablet, effervescent	Oral	NEUTEC İLAÇ SAN. TİC. A.Ş.	2010-12-02	Not applicable
ELUCEF PLUS 375/62.5 MG EFERVESAN TABLET, 20 ADET	Cefdinir (375 mg) + Clavulanate potassium (62.5 mg)	Tablet, effervescent	Oral	NEUTEC İLAÇ SAN. TİC. A.Ş.	2010-12-02	Not applicable

Chemical Identifiers

UNII: CI0FAO63WC
CAS number: 91832-40-5
InChI Key: RTXOFQZKPXMALH-GHXIOONMSA-N
InChI: InChI=1S/C14H13N5O5S2/c1-2-5-3-25-12-8(11(21)19(12)9(5)13(22)23)17-10(20)7(18-24)6-4-26-14(15)16-6/h2,4,8,12,24H,1,3H2,(H2,15,16)(H,17,20)(H,22,23)/b18-7-/t8-,12-/m1/s1
IUPAC Name: (6R,7R)-7-[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(N-hydroxyimino)acetamido]-3-ethenyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
SMILES: [H][C@]12SCC(C=C)=C(N1C(=O)[C@H]2NC(=O)C(=N/O)\C1=CSC(N)=N1)C(O)=O

References

Synthesis Reference

Gwan Sun Lee, Young Kil Chang, Jong Pil Chun, Joon Hyung Koh, "Process for preparation of cefdinir." U.S. Patent US6093814, issued December, 1995.

US6093814

General References

Kimura Y, Kawamura M, Owada M, Fujiwara T, Maesawa C, Hiramori K: Successful steroid therapy for cefdinir-induced acute tubulointerstitial nephritis with progressive renal failure. Intern Med. 2001 Feb;40(2):114-7. doi: 10.2169/internalmedicine.40.114. [Article]
Perry CM, Scott LJ: Cefdinir: a review of its use in the management of mild-to-moderate bacterial infections. Drugs. 2004;64(13):1433-64. doi: 10.2165/00003495-200464130-00004. [Article]
Guay DR: Pharmacodynamics and pharmacokinetics of cefdinir, an oral extended spectrum cephalosporin. Pediatr Infect Dis J. 2000 Dec;19(12 Suppl):S141-6. [Article]
Paris MM, Devcich KJ: Overview of cefdinir: pharmacokinetics, safety, and efficacy in the treatment of uncomplicated skin and skin structure infections. Cutis. 2004 May;73(5 Suppl):14-8. [Article]
Chen J, Ahmad J: Cefdinir-induced hepatotoxicity: potential hazards of inappropriate antibiotic use. J Gen Intern Med. 2008 Nov;23(11):1914-6. doi: 10.1007/s11606-008-0758-y. Epub 2008 Aug 28. [Article]
Sader HS, Biedenbach DJ, Streit JM, Jones RN: Cefdinir activity against contemporary North American isolates from community-acquired urinary tract infections. Int J Antimicrob Agents. 2005 Jan;25(1):89-92. doi: 10.1016/j.ijantimicag.2004.07.006. [Article]
Ochiai S, Sekiguchi S, Hayashi A, Shimadzu M, Ishiko H, Matsushima-Nishiwaki R, Kozawa O, Yasuda M, Deguchi T: Decreased affinity of mosaic-structure recombinant penicillin-binding protein 2 for oral cephalosporins in Neisseria gonorrhoeae. J Antimicrob Chemother. 2007 Jul;60(1):54-60. Epub 2007 May 31. [Article]
Ferrer-Gonzalez E, Kaul M, Parhi AK, LaVoie EJ, Pilch DS: beta-Lactam Antibiotics with a High Affinity for PBP2 Act Synergistically with the FtsZ-Targeting Agent TXA707 against Methicillin-Resistant Staphylococcus aureus. Antimicrob Agents Chemother. 2017 Aug 24;61(9). pii: AAC.00863-17. doi: 10.1128/AAC.00863-17. Print 2017 Sep. [Article]
Sanbongi Y, Suzuki T, Osaki Y, Senju N, Ida T, Ubukata K: Molecular evolution of beta-lactam-resistant Haemophilus influenzae: 9-year surveillance of penicillin-binding protein 3 mutations in isolates from Japan. Antimicrob Agents Chemother. 2006 Jul;50(7):2487-92. [Article]
Kumar P, Chauhan V, Silva JRA, Lameira J, d'Andrea FB, Li SG, Ginell SL, Freundlich JS, Alves CN, Bailey S, Cohen KA, Lamichhane G: Mycobacterium abscessus l,d-Transpeptidases Are Susceptible to Inactivation by Carbapenems and Cephalosporins but Not Penicillins. Antimicrob Agents Chemother. 2017 Sep 22;61(10). pii: AAC.00866-17. doi: 10.1128/AAC.00866-17. Print 2017 Oct. [Article]
Moore BA, Jevons S, Brammer KW: Peptidoglycan transpeptidase inhibition in Pseudomonas aeruginosa and Escherichia coli by Penicillins and Cephalosporins. Antimicrob Agents Chemother. 1979 Apr;15(4):513-7. doi: 10.1128/aac.15.4.513. [Article]
Prober CG: Cephalosporins: an update. Pediatr Rev. 1998 Apr;19(4):118-27. doi: 10.1542/pir.19-4-118. [Article]
Labro MT, el Benna J, Charlier N, Abdelghaffar H, Hakim J: Cefdinir (CI-983), a new oral amino-2-thiazolyl cephalosporin, inhibits human neutrophil myeloperoxidase in the extracellular medium but not the phagolysosome. J Immunol. 1994 Mar 1;152(5):2447-55. [Article]
FDA Approved Drug Products: Omnicef (cefdinir) [Link]
Pfizer MSDS, Cefdinir [Link]
Omnicef [Link]
Appropriate prescribing of beta-lactamase antibiotics [Link]
DailyMed: Cefdinir oral capsules [Link]

External Links

Human Metabolome Database: HMDB0014675
KEGG Drug: D00917
KEGG Compound: C08110
PubChem Compound: 6915944
PubChem Substance: 46505573
ChemSpider: 5291705
BindingDB: 50248190
RxNav: 25037
ChEBI: 3485
ChEMBL: CHEMBL927
ZINC: ZINC000003927198
Therapeutic Targets Database: DAP000436
PharmGKB: PA164768739
RxList: RxList Drug Page
Drugs.com: Drugs.com Drug Page
PDRhealth: PDRhealth Drug Page
Wikipedia: Cefdinir

MSDS

Download (57 KB)

Clinical Trials

Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">

Phase	Status	Purpose	Conditions	Count
4	Completed	Not Available	Healthy Subjects (HS)	3
4	Completed	Treatment	Acute Bacterial Sinusitis (ABS)	2
4	Completed	Treatment	Acute Otitis Media (AOM)	2
4	Completed	Treatment	Mild to Moderate Uncomplicated Skin and Skin Structure Infections	1
4	Completed	Treatment	Pneumonia	1

Pharmacoeconomics

Manufacturers

Aurobindo pharma ltd
Lupin ltd
Orchid healthcare
Sandoz inc
Teva pharmaceuticals usa
Abbott laboratories

Packagers

Abbott Laboratories Ltd.
A-S Medication Solutions LLC
Aurobindo Pharma Ltd.
Ceph International Corp.
DAVA Pharmaceuticals
Dispensing Solutions
Diversified Healthcare Services Inc.
Greenstone LLC
Lupin Pharmaceuticals Inc.
Murfreesboro Pharmaceutical Nursing Supply
Northstar Rx LLC
Orchid Healthcare
PD-Rx Pharmaceuticals Inc.
Physicians Total Care Inc.
Redpharm Drug
Resource Optimization and Innovation LLC
Sandoz
Southwood Pharmaceuticals
Teva Pharmaceutical Industries Ltd.

Dosage Forms

Form	Route	Strength
Suspension	Oral	250 mg/5ml
Tablet, film coated		300 mg
Tablet, film coated
Tablet, coated	Oral
Powder, for suspension	Oral	125 g
Powder, for suspension	Oral	5 g
Capsule	Oral	300 mg/1
Powder, for suspension	Oral	125 mg/5mL
Powder, for suspension	Oral	250 mg/5mL
Tablet, effervescent	Oral	600 mg
Tablet, coated		300 mg
Tablet, coated
Tablet, coated		600 mg
Capsule	Oral	300 mg
Tablet, effervescent	Oral
Tablet, effervescent	Oral	300 mg
Tablet, effervescent	Oral
Powder	Oral
Powder, for solution	Oral	125 mg
Powder, for solution	Oral	250 mg
Capsule, coated	Oral	500 mg
Capsule, coated	Oral	50000000 mg
Capsule	Oral
Tablet, film coated		600 mg
Suspension	Oral	1.500 g
Capsule	Oral	100 mg
Suspension	Oral	125 mg/5ml

Prices

Unit description	Cost	Unit
Omnicef 125 mg/5ml Suspension 100ml Bottle	101.59USD	bottle
Cefdinir 125 mg/5ml Suspension 60ml Bottle	53.05USD	bottle
Omnicef 300 mg capsule	6.31USD	capsule
Omnicef 300 mg omni-pac capsule	5.72USD	capsule
Cefdinir 300 mg capsule	5.22USD	capsule

DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.

Patents

Patent Number	Pediatric Extension	Approved	Expires (estimated)	Region
US4935507	No	1990-06-19	2011-12-04

Properties

State

Solid

Experimental Properties

Property	Value	Source
melting point (°C)	>135	https://www.trc-canada.com/product-detail/?CatNum=C242670
boiling point (°C)	708.82	https://cymitquimica.com/products/45-1097614/213978-34-8/cefdinir/
water solubility	8.85 ± 0.87 mg/mL	https://www.mdpi.com/1420-3049/22/2/280/htm
logP	-3.47	https://aac.asm.org/content/47/2/689
pKa	9.7	https://www.chemicalbook.com/ChemicalProductProperty_US_CB7483101.aspx

Predicted Properties

Property	Value	Source
Water Solubility	0.0878 mg/mL	ALOGPS
logP	0.02	ALOGPS
logP	-0.89	Chemaxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	2.73	Chemaxon
pKa (Strongest Basic)	3.61	Chemaxon
Physiological Charge	-1	Chemaxon
Hydrogen Acceptor Count	8	Chemaxon
Hydrogen Donor Count	4	Chemaxon
Polar Surface Area	158.21 Å²	Chemaxon
Rotatable Bond Count	5	Chemaxon
Refractivity	94.34 m³·mol^-1	Chemaxon
Polarizability	36.14 Å³	Chemaxon
Number of Rings	3	Chemaxon
Bioavailability	1	Chemaxon
Rule of Five	Yes	Chemaxon
Ghose Filter	No	Chemaxon
Veber's Rule	No	Chemaxon
MDDR-like Rule	No	Chemaxon

Predicted ADMET Features

Property	Value	Probability
Human Intestinal Absorption	-	0.7692
Blood Brain Barrier	-	0.9659
Caco-2 permeable	-	0.7205
P-glycoprotein substrate	Non-substrate	0.5185
P-glycoprotein inhibitor I	Non-inhibitor	0.9298
P-glycoprotein inhibitor II	Non-inhibitor	0.9165
Renal organic cation transporter	Non-inhibitor	0.8919
CYP450 2C9 substrate	Non-substrate	0.8676
CYP450 2D6 substrate	Non-substrate	0.8203
CYP450 3A4 substrate	Non-substrate	0.5821
CYP450 1A2 substrate	Non-inhibitor	0.7603
CYP450 2C9 inhibitor	Non-inhibitor	0.8303
CYP450 2D6 inhibitor	Non-inhibitor	0.894
CYP450 2C19 inhibitor	Non-inhibitor	0.8044
CYP450 3A4 inhibitor	Non-inhibitor	0.8436
CYP450 inhibitory promiscuity	Low CYP Inhibitory Promiscuity	0.953
Ames test	Non AMES toxic	0.6686
Carcinogenicity	Non-carcinogens	0.8339
Biodegradation	Not ready biodegradable	0.9925
Rat acute toxicity	1.8801 LD50, mol/kg	Not applicable
hERG inhibition (predictor I)	Weak inhibitor	0.9878
hERG inhibition (predictor II)	Non-inhibitor	0.8964

ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)

Not Available

Spectra

Spectrum	Spectrum Type	Splash Key
Predicted GC-MS Spectrum - GC-MS	Predicted GC-MS	splash10-0006-4922000000-dc82c787eb5267828736
LC-MS/MS Spectrum - LC-ESI-qTof , Positive	LC-MS/MS	splash10-004i-2983000000-72bf1ac3398fbaa1531b
MS/MS Spectrum - , positive	LC-MS/MS	splash10-004i-2983000000-72bf1ac3398fbaa1531b
Predicted MS/MS Spectrum - 10V, Positive (Annotated)	Predicted LC-MS/MS	splash10-002b-0119000000-4360db8ee8f9b5c5f1a3
Predicted MS/MS Spectrum - 10V, Negative (Annotated)	Predicted LC-MS/MS	splash10-004i-1492000000-e0d04a44bb5cccab2389
Predicted MS/MS Spectrum - 20V, Positive (Annotated)	Predicted LC-MS/MS	splash10-0h03-0915000000-6cd406eb5313aeebdf25
Predicted MS/MS Spectrum - 20V, Negative (Annotated)	Predicted LC-MS/MS	splash10-01b9-2924000000-c8d3edc09b18408540b8
Predicted MS/MS Spectrum - 40V, Positive (Annotated)	Predicted LC-MS/MS	splash10-0330-0914000000-73164ae882b25debe1e0
Predicted MS/MS Spectrum - 40V, Negative (Annotated)	Predicted LC-MS/MS	splash10-00di-4902000000-5b67bda2ed08c22a5da5
Predicted 1H NMR Spectrum	1D NMR	Not Applicable
Predicted 13C NMR Spectrum	1D NMR	Not Applicable

Chromatographic Properties

Collision Cross Sections (CCS)

Adduct	CCS Value (Å²)	Source type	Source
[M-H]-	204.5422026	predicted	DarkChem Lite v0.1.0
[M-H]-	201.9678026	predicted	DarkChem Lite v0.1.0
[M-H]-	184.04483	predicted	DeepCCS 1.0 (2019)
[M+H]+	204.1108026	predicted	DarkChem Lite v0.1.0
[M+H]+	201.9001026	predicted	DarkChem Lite v0.1.0
[M+H]+	186.44038	predicted	DeepCCS 1.0 (2019)
[M+Na]+	204.7441026	predicted	DarkChem Lite v0.1.0
[M+Na]+	192.64024	predicted	DeepCCS 1.0 (2019)

Targets

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Details1. Penicillin-binding protein 2

Kind: Protein
Organism: Neisseria gonorrhoeae
Pharmacological action: Yes
Actions: Inhibitor

General Function: Penicillin binding
Specific Function: Synthesis of cross-linked peptidoglycan from the lipid intermediates.
Gene Name: penA
Uniprot ID: P08149
Uniprot Name: Penicillin-binding protein 2
Molecular Weight: 63649.54 Da

References

Ochiai S, Sekiguchi S, Hayashi A, Shimadzu M, Ishiko H, Matsushima-Nishiwaki R, Kozawa O, Yasuda M, Deguchi T: Decreased affinity of mosaic-structure recombinant penicillin-binding protein 2 for oral cephalosporins in Neisseria gonorrhoeae. J Antimicrob Chemother. 2007 Jul;60(1):54-60. Epub 2007 May 31. [Article]
Ferrer-Gonzalez E, Kaul M, Parhi AK, LaVoie EJ, Pilch DS: beta-Lactam Antibiotics with a High Affinity for PBP2 Act Synergistically with the FtsZ-Targeting Agent TXA707 against Methicillin-Resistant Staphylococcus aureus. Antimicrob Agents Chemother. 2017 Aug 24;61(9). pii: AAC.00863-17. doi: 10.1128/AAC.00863-17. Print 2017 Sep. [Article]

Details2. PBP3

Kind: Protein
Organism: Haemophilus influenzae
Pharmacological action: Yes
Actions: Inhibitor

General Function: Penicillin binding
Specific Function: Not Available
Gene Name: pbp3
Uniprot ID: Q60FT7
Uniprot Name: PBP3
Molecular Weight: 67295.025 Da

References

Sanbongi Y, Suzuki T, Osaki Y, Senju N, Ida T, Ubukata K: Molecular evolution of beta-lactam-resistant Haemophilus influenzae: 9-year surveillance of penicillin-binding protein 3 mutations in isolates from Japan. Antimicrob Agents Chemother. 2006 Jul;50(7):2487-92. [Article]
Ferrer-Gonzalez E, Kaul M, Parhi AK, LaVoie EJ, Pilch DS: beta-Lactam Antibiotics with a High Affinity for PBP2 Act Synergistically with the FtsZ-Targeting Agent TXA707 against Methicillin-Resistant Staphylococcus aureus. Antimicrob Agents Chemother. 2017 Aug 24;61(9). pii: AAC.00863-17. doi: 10.1128/AAC.00863-17. Print 2017 Sep. [Article]
Tristram S, Jacobs MR, Appelbaum PC: Antimicrobial resistance in Haemophilus influenzae. Clin Microbiol Rev. 2007 Apr;20(2):368-89. doi: 10.1128/CMR.00040-06. [Article]

Details3. Myeloperoxidase

Kind: Protein
Organism: Humans
Pharmacological action: No
Actions: Inhibitor

General Function: Peroxidase activity
Specific Function: Part of the host defense system of polymorphonuclear leukocytes. It is responsible for microbicidal activity against a wide range of organisms. In the stimulated PMN, MPO catalyzes the production o...
Gene Name: MPO
Uniprot ID: P05164
Uniprot Name: Myeloperoxidase
Molecular Weight: 83867.71 Da

References

Labro MT, el Benna J, Charlier N, Abdelghaffar H, Hakim J: Cefdinir (CI-983), a new oral amino-2-thiazolyl cephalosporin, inhibits human neutrophil myeloperoxidase in the extracellular medium but not the phagolysosome. J Immunol. 1994 Mar 1;152(5):2447-55. [Article]

4. Peptidoglycan transpeptidase

Kind

Group

Organism

Not Available

Pharmacological action

Unknown

Actions

Inhibitor

The enzyme peptidoglycan transpeptidase, which catalyzes cell wall cross-linking of bacteria.

References

Kumar P, Chauhan V, Silva JRA, Lameira J, d'Andrea FB, Li SG, Ginell SL, Freundlich JS, Alves CN, Bailey S, Cohen KA, Lamichhane G: Mycobacterium abscessus l,d-Transpeptidases Are Susceptible to Inactivation by Carbapenems and Cephalosporins but Not Penicillins. Antimicrob Agents Chemother. 2017 Sep 22;61(10). pii: AAC.00866-17. doi: 10.1128/AAC.00866-17. Print 2017 Oct. [Article]
Moore BA, Jevons S, Brammer KW: Peptidoglycan transpeptidase inhibition in Pseudomonas aeruginosa and Escherichia coli by Penicillins and Cephalosporins. Antimicrob Agents Chemother. 1979 Apr;15(4):513-7. doi: 10.1128/aac.15.4.513. [Article]

Transporters

Details1. Solute carrier family 22 member 5

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Inhibitor

General Function: Symporter activity
Specific Function: Sodium-ion dependent, high affinity carnitine transporter. Involved in the active cellular uptake of carnitine. Transports one sodium ion with one molecule of carnitine. Also transports organic cat...
Gene Name: SLC22A5
Uniprot ID: O76082
Uniprot Name: Solute carrier family 22 member 5
Molecular Weight: 62751.08 Da

References

Ganapathy ME, Huang W, Rajan DP, Carter AL, Sugawara M, Iseki K, Leibach FH, Ganapathy V: beta-lactam antibiotics as substrates for OCTN2, an organic cation/carnitine transporter. J Biol Chem. 2000 Jan 21;275(3):1699-707. [Article]
Tein I: Carnitine transport: pathophysiology and metabolism of known molecular defects. J Inherit Metab Dis. 2003;26(2-3):147-69. [Article]
HMDB database, Cefdinir [Link]

Details2. Solute carrier family 15 member 1

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Substrate
Inhibitor

General Function: Proton-dependent oligopeptide secondary active transmembrane transporter activity
Specific Function: Proton-coupled intake of oligopeptides of 2 to 4 amino acids with a preference for dipeptides. May constitute a major route for the absorption of protein digestion end-products.
Gene Name: SLC15A1
Uniprot ID: P46059
Uniprot Name: Solute carrier family 15 member 1
Molecular Weight: 78805.265 Da

References

Ganapathy ME, Prasad PD, Mackenzie B, Ganapathy V, Leibach FH: Interaction of anionic cephalosporins with the intestinal and renal peptide transporters PEPT 1 and PEPT 2. Biochim Biophys Acta. 1997 Mar 13;1324(2):296-308. [Article]
Terada T, Saito H, Mukai M, Inui K: Recognition of beta-lactam antibiotics by rat peptide transporters, PEPT1 and PEPT2, in LLC-PK1 cells. Am J Physiol. 1997 Nov;273(5 Pt 2):F706-11. [Article]
Tsuji A: Transporter-mediated Drug Interactions. Drug Metab Pharmacokinet. 2002;17(4):253-74. [Article]

Details3. Solute carrier family 15 member 2

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Inhibitor

General Function: Peptide:proton symporter activity
Specific Function: Proton-coupled intake of oligopeptides of 2 to 4 amino acids with a preference for dipeptides.
Gene Name: SLC15A2
Uniprot ID: Q16348
Uniprot Name: Solute carrier family 15 member 2
Molecular Weight: 81782.77 Da

References

Ganapathy ME, Prasad PD, Mackenzie B, Ganapathy V, Leibach FH: Interaction of anionic cephalosporins with the intestinal and renal peptide transporters PEPT 1 and PEPT 2. Biochim Biophys Acta. 1997 Mar 13;1324(2):296-308. [Article]
Terada T, Saito H, Mukai M, Inui K: Recognition of beta-lactam antibiotics by rat peptide transporters, PEPT1 and PEPT2, in LLC-PK1 cells. Am J Physiol. 1997 Nov;273(5 Pt 2):F706-11. [Article]

Details4. Solute carrier family 22 member 6

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Substrate
Curator comments: Data in the literature regarding this transporter action for this drug are limited.

General Function: Sodium-independent organic anion transmembrane transporter activity
Specific Function: Involved in the renal elimination of endogenous and exogenous organic anions. Functions as organic anion exchanger when the uptake of one molecule of organic anion is coupled with an efflux of one ...
Gene Name: SLC22A6
Uniprot ID: Q4U2R8
Uniprot Name: Solute carrier family 22 member 6
Molecular Weight: 61815.78 Da

References

Kim YC, Kim IB, Noh CK, Quach HP, Yoon IS, Chow ECY, Kim M, Jin HE, Cho KH, Chung SJ, Pang KS, Maeng HJ: Effects of 1alpha,25-dihydroxyvitamin D3 , the natural vitamin D receptor ligand, on the pharmacokinetics of cefdinir and cefadroxil, organic anion transporter substrates, in rat. J Pharm Sci. 2014 Nov;103(11):3793-3805. doi: 10.1002/jps.24195. Epub 2014 Sep 29. [Article]

Details5. Solute carrier family 22 member 8

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Substrate
Curator comments: Data in the literature regarding this transporter action for this drug are limited.

General Function: Sodium-independent organic anion transmembrane transporter activity
Specific Function: Plays an important role in the excretion/detoxification of endogenous and exogenous organic anions, especially from the brain and kidney. Involved in the transport basolateral of steviol, fexofenad...
Gene Name: SLC22A8
Uniprot ID: Q8TCC7
Uniprot Name: Solute carrier family 22 member 8
Molecular Weight: 59855.585 Da

References

Wang H, Sun P, Wang C, Meng Q, Liu Z, Huo X, Sun H, Ma X, Peng J, Liu K: Pharmacokinetic changes of cefdinir and cefditoren and its molecular mechanisms in acute kidney injury in rats. J Pharm Pharmacol. 2018 Nov;70(11):1503-1512. doi: 10.1111/jphp.12994. Epub 2018 Jul 25. [Article]
Kim YC, Kim IB, Noh CK, Quach HP, Yoon IS, Chow ECY, Kim M, Jin HE, Cho KH, Chung SJ, Pang KS, Maeng HJ: Effects of 1alpha,25-dihydroxyvitamin D3 , the natural vitamin D receptor ligand, on the pharmacokinetics of cefdinir and cefadroxil, organic anion transporter substrates, in rat. J Pharm Sci. 2014 Nov;103(11):3793-3805. doi: 10.1002/jps.24195. Epub 2014 Sep 29. [Article]
Ueo H, Motohashi H, Katsura T, Inui K: Human organic anion transporter hOAT3 is a potent transporter of cephalosporin antibiotics, in comparison with hOAT1. Biochem Pharmacol. 2005 Oct 1;70(7):1104-13. doi: 10.1016/j.bcp.2005.06.024. [Article]

Drug created at June 13, 2005 13:24 / Updated at November 03, 2023 23:43

Cefdinir

Identification

Structure for Cefdinir (DB00535)

Pharmacology

Interactions

Products

Categories

Chemical Identifiers

References

Clinical Trials

Pharmacoeconomics

Properties

Spectra

Collision Cross Sections (CCS)

Targets

References

References

References

References

Transporters

References

References

References

References

References