Spiramycin

Identification

Summary

Spiramycin is a macrolide antimicrobial agent used in the treatment of various bacterial infections.

Brand Names

Rovamycin

Generic Name

Spiramycin

DrugBank Accession Number

DB06145

Background

Spiramycin is a primarily bacteriostatic macrolide antimicrobial agent with activity against Gram-positive cocci and rods, Gram-negative cocci and also Legionellae, mycoplasmas, chlamydiae, some types of spirochetes, Toxoplasma gondii and Cryptosporidium. Spiramycin is a 16-membered ring macrolide discovered in 1952 as a product of Streptomyces ambofaciens that has been available in oral formulations since 1955, and parenteral formulations since 1987. Resistant organisms include Enterobacteria, pseudomonads, and moulds.

Type

Small Molecule

Groups

Approved

Structure

Similar Structures

Weight: Average: 843.065
Monoisotopic: 842.514005071
Chemical Formula: C₄₃H₇₄N₂O₁₄

Synonyms

Demycarosylturimycin H
Foromacidin A
Foromacidine A
Spiramycin 1
Spiramycin A
Spiramycin I

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Pharmacology

Indication

Macrolide antibiotic for treatment of various infections.

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Associated Conditions

Indication Type	Indication	Combined Product Details	Approval Level	Age Group	Patient Characteristics	Dose Form
Treatment of	Bacterial infection		••••••••••••

Contraindications & Blackbox Warnings

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Pharmacodynamics

The absolute bioavailability of oral spiramycin is generally within the range of 30 to 40%. After a 1 g oral dose, the maximum serum drug concentration was found to be within the range 0.4 to 1.4 mg/L.

Mechanism of action

The mechanism of action of macrolides has been a matter of controversy for some time. Spiramycin, a 16-membered macrolide, inhibits translocation by binding to bacterial 50S ribosomal subunits with an apparent 1 : 1 stoichiometry. This antibiotic is a potent inhibitor of the binding to the ribosome of both donor and acceptor substrates. The primary mechanism of action is done by stimulation of dissociation of peptidyl-tRNA from ribosomes during translocation.I

Target	Actions	Organism
A50S ribosomal protein L3	antagonist inhibitor	Streptococcus pyogenes serotype M1

Absorption

The extent of absorption of Spiramycin was shown to be incomplete. Oral bioavailability ranges from 30-39%. Spiramycin has slower rate of absorption than Erythromycin. It has a high pKa (7.9) which could be a result of high degree of ionization in acidic medium of the stomach.

Volume of distribution

The tissue distribution of spiramycin is extensive. The volume of distribution is in excess of 300 L, and concentrations achieved in bone, muscle, respiratory tract and saliva exceed those found in serum. Spiramycin showed high concentrations in tissues such as: lungs, bronchi, tonsils, and sinuses.

Protein binding

Low level of protein binding (10-25%).

Metabolism

Spiramycin is less metabolised than some of the other macrolides. Metabolism has not been well studied. It is mainly done in the liver to the active metabolites.

Route of elimination

Fecal-biliary route is the primary route of elimination. The secondary route is renal-urinary route.

Half-life

Intravenous: Young persons (18 to 32 years of age): Approximately 4.5 to 6.2 hours. Elderly persons (73 to 85 years of age): Approximately 9.8 to 13.5 hours.

Oral: 5.5-8 hours, Rectal in children: 8 hours

Clearance

80% of the administered dose excreted in the bile, which makes the fecal-biliary route is the most important route of elimination. Enterohepatic recycling could also occur. Only 4 to 14% of an administered dose is eliminated through renal-urinary excretion route.

Adverse Effects

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Toxicity

Cardiac toxicity, specifically QT prolongation (irregular heartbeat; recurrent fainting).
Cholestatic hepatitis (abdominal pain; nausea; vomiting; yellow eyes or skin).
Gastrointestinal toxicity, specifically acute colitis (abdominal pain and tenderness; bloody stools; fever).
Intestinal injury (abdominal pain and tenderness). Ulcerated esophagitis (chest pain; heartburn).

Pathways

Not Available

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Not Available

Interactions

Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">

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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Acenocoumarol	The risk or severity of bleeding can be increased when Spiramycin is combined with Acenocoumarol.
Ambroxol	The risk or severity of methemoglobinemia can be increased when Spiramycin is combined with Ambroxol.
Articaine	The risk or severity of methemoglobinemia can be increased when Spiramycin is combined with Articaine.
Atorvastatin	The risk or severity of adverse effects can be increased when Spiramycin is combined with Atorvastatin.
BCG vaccine	The therapeutic efficacy of BCG vaccine can be decreased when used in combination with Spiramycin.

Food Interactions

No food interactions are expected.

Products

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Brand Name Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End	Region	Image
Rovamycine 250 Capsule 750000 Unit	Capsule	750000 unit	Oral	Odan Laboratories Ltd	1957-12-31	Not applicable
Rovamycine 500 Capsule 1500000 Unit	Capsule	1500000 unit	Oral	Odan Laboratories Ltd	1957-12-31	Not applicable

Mixture Products

Name	Ingredients	Dosage	Route	Labeller	Marketing Start	Marketing End	Region	Image
METİRASİN 1,5 MIU/250 MG FILM TABLET, 10 ADET	Spiramycin (1.5 IU) + Metronidazole (250 mg)	Tablet, film coated		VEM İLAÇ SAN. VE TİC. A.Ş.	2012-01-25	Not applicable
METİRASİN 1,5 MIU/250 MG FILM TABLET, 14 ADET	Spiramycin (1.5 IU) + Metronidazole (250 mg)	Tablet, film coated		VEM İLAÇ SAN. VE TİC. A.Ş.	2012-01-25	Not applicable

Chemical Identifiers

UNII: 033ECH6IFG
CAS number: 24916-50-5
InChI Key: ACTOXUHEUCPTEW-CEUOBAOPSA-N
InChI: InChI=1S/C43H74N2O14/c1-24-21-29(19-20-46)39(59-42-37(49)36(45(9)10)38(27(4)56-42)58-35-23-43(6,51)41(50)28(5)55-35)40(52-11)31(47)22-33(48)53-25(2)15-13-12-14-16-32(24)57-34-18-17-30(44(7)8)26(3)54-34/h12-14,16,20,24-32,34-42,47,49-51H,15,17-19,21-23H2,1-11H3/b13-12+,16-14+/t24-,25-,26-,27-,28+,29+,30+,31-,32+,34+,35+,36-,37-,38-,39+,40+,41+,42+,43-/m1/s1
IUPAC Name: 2-[(4R,5S,6S,7R,9R,10R,11E,13E,16R)-6-{[(2S,3R,4R,5S,6R)-5-{[(2S,4R,5S,6S)-4,5-dihydroxy-4,6-dimethyloxan-2-yl]oxy}-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy}-10-{[(2R,5S,6R)-5-(dimethylamino)-6-methyloxan-2-yl]oxy}-4-hydroxy-5-methoxy-9,16-dimethyl-2-oxo-1-oxacyclohexadeca-11,13-dien-7-yl]acetaldehyde
SMILES: [H][C@@]1(CC[C@@H]([C@@H](C)O1)N(C)C)O[C@H]1\C=C\C=C\C[C@@H](C)OC(=O)C[C@@H](O)[C@H](OC)[C@@H](O[C@]2([H])O[C@H](C)[C@@H](O[C@@]3([H])C[C@@](C)(O)[C@@H](O)[C@H](C)O3)[C@@H]([C@H]2O)N(C)C)[C@@H](CC=O)C[C@H]1C

References

General References

article [Link]
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product info [Link]

External Links

PubChem Compound: 6440717
PubChem Substance: 347827756
ChemSpider: 4451378
RxNav: 9991
ChEBI: 85260
ChEMBL: CHEMBL453514
ZINC: ZINC000257373089
PDBe Ligand: SPR
Wikipedia: Spiramycin

PDB Entries

1kd1 / 5igz

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	Recruiting	Treatment	Toxoplasmosis	1
3	Completed	Treatment	Toxoplasmosis, Congenital	1
1	Completed	Treatment	Cryptosporidiosis infection / Human Immunodeficiency Virus (HIV) Infections	1
Not Available	Completed	Treatment	Cryptosporidiosis infection / Human Immunodeficiency Virus (HIV) Infections	1

Pharmacoeconomics

Manufacturers

Not Available

Packagers

Not Available

Dosage Forms

Form	Route	Strength
Injection, powder, for solution	Parenteral	1.5 miu
Tablet, film coated	Oral	3000.000 iu
Tablet, coated	Oral	3 million IU
Tablet, coated	Oral	3 million unit
Tablet, film coated
Tablet	Oral
Tablet; tablet, film coated	Oral
Tablet, film coated	Oral	3 miu
Tablet	Oral	1500000 UI
Tablet	Oral	450 mg
Capsule	Oral	750000 unit
Capsule	Oral	1500000 unit
Syrup	Oral
Tablet, film coated	Oral	3000.000 UI
Tablet, film coated	Oral
Tablet, film coated	Oral	3000.000 i.u.
Tablet, film coated	Oral	1.5 miu
Tablet	Oral
Powder
Capsule	Oral	500 mg
Tablet, film coated	Oral	500 mg
Syrup	Oral	125 mg/5ml

Prices

Not Available

Patents

Not Available

Properties

State

Solid

Experimental Properties

Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.196 mg/mL	ALOGPS
logP	2.99	ALOGPS
logP	2.5	Chemaxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	12.53	Chemaxon
pKa (Strongest Basic)	9.33	Chemaxon
Physiological Charge	2	Chemaxon
Hydrogen Acceptor Count	15	Chemaxon
Hydrogen Donor Count	4	Chemaxon
Polar Surface Area	195.38 Å²	Chemaxon
Rotatable Bond Count	11	Chemaxon
Refractivity	219.25 m³·mol^-1	Chemaxon
Polarizability	93.01 Å³	Chemaxon
Number of Rings	4	Chemaxon
Bioavailability	0	Chemaxon
Rule of Five	No	Chemaxon
Ghose Filter	No	Chemaxon
Veber's Rule	No	Chemaxon
MDDR-like Rule	Yes	Chemaxon

Predicted ADMET Features

Not Available

Spectra

Mass Spec (NIST)

Not Available

Spectra

Spectrum	Spectrum Type	Splash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)	Predicted LC-MS/MS	splash10-0006-0400001090-169887a0cd83c94e536d
Predicted MS/MS Spectrum - 10V, Negative (Annotated)	Predicted LC-MS/MS	splash10-0006-0300002090-e61a58c15c8c88fca4df
Predicted MS/MS Spectrum - 20V, Positive (Annotated)	Predicted LC-MS/MS	splash10-0006-2700000290-103e9f21278e96e004a3
Predicted MS/MS Spectrum - 20V, Negative (Annotated)	Predicted LC-MS/MS	splash10-000x-0800009270-6cd6ba7dfc2de1d9d39c
Predicted MS/MS Spectrum - 40V, Positive (Annotated)	Predicted LC-MS/MS	splash10-006y-3910050010-366ab80dce8b49397217
Predicted MS/MS Spectrum - 40V, Negative (Annotated)	Predicted LC-MS/MS	splash10-0a4i-0210093110-71c5603efe5d432b794d

Chromatographic Properties