Raltegravir

Identification

Summary

Raltegravir is an antiretroviral agent used for the treatment of HIV infections in conjunction with other antiretrovirals.

Brand Names

Isentress

Generic Name

Raltegravir

DrugBank Accession Number

DB06817

Background

Raltegravir is an antiretroviral drug produced by Merck & Co., used to treat HIV infection. It received approval by the U.S. Food and Drug Administration (FDA) on 12 October 2007, the first of a new class of HIV drugs, the integrase inhibitors, to receive such approval.

Type

Small Molecule

Groups

Approved

Structure

3D

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MOLSDF3D-SDFPDBSMILESInChI

Similar Structures

Structure for Raltegravir (DB06817)

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Weight

Average: 444.4163
Monoisotopic: 444.155746017

Chemical Formula

C₂₀H₂₁FN₆O₅

Synonyms

• Raltegravir

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Pharmacology

Indication

For the treatment of HIV-1 infection in conjunction with other antiretrovirals.

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Associated Conditions

Indication Type	Indication	Combined Product Details	Approval Level	Age Group	Patient Characteristics	Dose Form
Used in combination to treat	Human immunodeficiency virus type 1 (hiv-1) infection		••••••••••••	•••••••••	•••• •••••• •• ••	••••••••••• ••••••• ••••••••• ••••••• •••• ••••••
Used in combination to treat	Human immunodeficiency virus type 1 (hiv-1) infection		••••••••••••	•••••		••••••••••• ••••••• ••••••••• ••••••• •••• ••••••

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Associated Therapies

• Post-exposure prophylaxis for occupational exposure to HIV therapy

Contraindications & Blackbox Warnings

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Pharmacodynamics

Not Available

Mechanism of action

Raltegravir inhibits HIV integrase to prevent the viral genome being incorporated into the human genome. Raltegravir is primarily metabolized by glucuronidation.

Target	Actions	Organism
AIntegrase	inhibitor	Human immunodeficiency virus 1

Absorption

Absorbed from the gastrointestinal tract.

Volume of distribution

Approximately 83% bound to human plasma protein and is minimally distributed into red blood cells (blood-to-plasma partitioning ratio of 0.6).

Protein binding

83%

Metabolism

Hepatic (UGT1A1)

Route of elimination

Feces and urine

Half-life

9 hours

Clearance

The major mechanism of clearance of raltegravir in humans is glucuronidation mediated by UGT1A1, the renal clearance of unchanged drug is a minor pathway of elimination of raltegravir (9% of total dose).

Adverse Effects

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Toxicity

Not Available

Pathways

Not Available

Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">

Not Available

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.

• Approved
• Vet approved
• Nutraceutical
• Illicit
• Withdrawn
• Investigational
• Experimental
• All Drugs

Drug	Interaction
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Acipimox	The risk or severity of myopathy, rhabdomyolysis, and myoglobinuria can be increased when Raltegravir is combined with Acipimox.
Adenine	The metabolism of Raltegravir can be decreased when combined with Adenine.
Adenovirus type 7 vaccine live	The therapeutic efficacy of Adenovirus type 7 vaccine live can be decreased when used in combination with Raltegravir.
Alendronic acid	The risk or severity of myopathy, rhabdomyolysis, and myoglobinuria can be increased when Alendronic acid is combined with Raltegravir.
Almasilate	The serum concentration of Raltegravir can be decreased when it is combined with Almasilate.

Food Interactions

• Take with or without food.

Products

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Product Ingredients

Ingredient	UNII	CAS	InChI Key
Raltegravir potassium	43Y000U234	871038-72-1	IFUKBHBISRAZTF-UHFFFAOYSA-M

Product Images

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Brand Name Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End	Region	Image
Isentress	Granule	100 mg	Oral	Merck Sharp & Dohme B.V.	2020-12-16	Not applicable
Isentress	Tablet, film coated	400 mg/1	Oral	Nucare Pharmaceuticals,inc.	2007-10-12	Not applicable
Isentress	Tablet	400 mg	Oral	Merck Ltd.	2007-11-28	Not applicable
Isentress	Tablet, film coated	400 mg	Oral	Merck Sharp & Dohme B.V.	2020-12-16	Not applicable
Isentress	Tablet, film coated	400 mg/1	Oral	A-S Medication Solutions	2007-10-12	Not applicable

Mixture Products

Name	Ingredients	Dosage	Route	Labeller	Marketing Start	Marketing End	Region	Image
DUTREBIS	Raltegravir (300 MG) + Lamivudine (150 MG)	Tablet, film coated	Oral	Organon Pharma (Uk) Limited	2015-06-27	2022-08-19

Categories

ATC Codes

J05AR16 — Lamivudine and raltegravir

• J05AR — Antivirals for treatment of HIV infections, combinations
• J05A — DIRECT ACTING ANTIVIRALS
• J05 — ANTIVIRALS FOR SYSTEMIC USE
• J — ANTIINFECTIVES FOR SYSTEMIC USE

J05AJ01 — Raltegravir

• J05AJ — Integrase inhibitors
• J05A — DIRECT ACTING ANTIVIRALS
• J05 — ANTIVIRALS FOR SYSTEMIC USE
• J — ANTIINFECTIVES FOR SYSTEMIC USE

Drug Categories

• Agents Causing Muscle Toxicity
• Anti-HIV Agents
• Anti-Infective Agents
• Anti-Retroviral Agents
• Antiinfectives for Systemic Use
• Antiviral Agents
• Antivirals for Systemic Use
• Antivirals used in combination for the treatment of HIV infections
• Direct Acting Antivirals
• Enzyme Inhibitors
• HIV Integrase Inhibitors
• Human Immunodeficiency Virus Integrase Strand Transfer Inhibitor
• Integrase Inhibitors
• Pyrrolidines
• Pyrrolidinones
• UGT1A1 Substrates

Chemical TaxonomyProvided by Classyfire

Description

This compound belongs to the class of organic compounds known as pyrimidinecarboxylic acids and derivatives. These are compounds containing a pyrimidine ring which bears a carboxylic acid group (or a derivative thereof).

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Diazines

Sub Class

Pyrimidines and pyrimidine derivatives

Direct Parent

Pyrimidinecarboxylic acids and derivatives

Alternative Parents

2-heteroaryl carboxamides / Pyrimidones / Fluorobenzenes / Hydroxypyrimidines / Aryl fluorides / Hydropyrimidines / Vinylogous acids / 1,3,4-oxadiazoles / Heteroaromatic compounds / Secondary carboxylic acid amides / Lactams / Azacyclic compounds / Oxacyclic compounds / Organofluorides / Hydrocarbon derivatives / Organonitrogen compounds / Organooxygen compounds / Organopnictogen compounds / Organic oxides

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Substituents

1,3,4-oxadiazole / 2-heteroaryl carboxamide / Aromatic heteromonocyclic compound / Aryl fluoride / Aryl halide / Azacycle / Azole / Benzenoid / Carboxamide group / Carboxylic acid derivative / Fluorobenzene / Halobenzene / Heteroaromatic compound / Hydrocarbon derivative / Hydropyrimidine / Hydroxypyrimidine / Lactam / Monocyclic benzene moiety / Organic nitrogen compound / Organic oxide / Organic oxygen compound / Organofluoride / Organohalogen compound / Organonitrogen compound / Organooxygen compound / Organopnictogen compound / Oxacycle / Oxadiazole / Pyrimidine-6-carboxylic acid or derivatives / Pyrimidone / Secondary carboxylic acid amide / Vinylogous acid

show 22 more

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

organofluorine compound, pyrimidines, 1,2,4-oxadiazole, dicarboxylic acid amide (CHEBI:82960)

Affected organisms

• Human Immunodeficiency Virus

Chemical Identifiers

UNII

22VKV8053U

CAS number

518048-05-0

InChI Key

CZFFBEXEKNGXKS-UHFFFAOYSA-N

InChI

InChI=1S/C20H21FN6O5/c1-10-25-26-17(32-10)16(30)24-20(2,3)19-23-13(14(28)18(31)27(19)4)15(29)22-9-11-5-7-12(21)8-6-11/h5-8,28H,9H2,1-4H3,(H,22,29)(H,24,30)

IUPAC Name

N-[(4-fluorophenyl)methyl]-5-hydroxy-1-methyl-2-{2-[(5-methyl-1,3,4-oxadiazol-2-yl)formamido]propan-2-yl}-6-oxo-1,6-dihydropyrimidine-4-carboxamide

SMILES

CN1C(=O)C(O)=C(N=C1C(C)(C)NC(=O)C1=NN=C(C)O1)C(=O)NCC1=CC=C(F)C=C1

References

General References

1. Nachman S, Zheng N, Acosta EP, Teppler H, Homony B, Graham B, Fenton T, Xu X, Wenning L, Spector SA, Frenkel LM, Alvero C, Worrell C, Handelsman E, Wiznia A: Pharmacokinetics, safety, and 48-week efficacy of oral raltegravir in HIV-1-infected children aged 2 through 18 years. Clin Infect Dis. 2014 Feb;58(3):413-22. doi: 10.1093/cid/cit696. Epub 2013 Oct 21. [Article]
2. Barau C, Furlan V, Yazdanpanah Y, Fagard C, Molina JM, Taburet AM, Barrail-Tran A: Characterization of binding of raltegravir to plasma proteins. Antimicrob Agents Chemother. 2013 Oct;57(10):5147-50. doi: 10.1128/AAC.00625-13. Epub 2013 Jul 15. [Article]
3. Arora R, de Beauchene IC, Polanski J, Laine E, Tchertanov L: Raltegravir flexibility and its impact on recognition by the HIV-1 IN targets. J Mol Recognit. 2013 Sep;26(9):383-401. doi: 10.1002/jmr.2277. [Article]
4. Eron JJ, Cooper DA, Steigbigel RT, Clotet B, Gatell JM, Kumar PN, Rockstroh JK, Schechter M, Markowitz M, Yeni P, Loutfy MR, Lazzarin A, Lennox JL, Strohmaier KM, Wan H, Barnard RJ, Nguyen BY, Teppler H: Efficacy and safety of raltegravir for treatment of HIV for 5 years in the BENCHMRK studies: final results of two randomised, placebo-controlled trials. Lancet Infect Dis. 2013 Jul;13(7):587-96. doi: 10.1016/S1473-3099(13)70093-8. Epub 2013 May 7. [Article]
5. Winston A, Mallon PW, Boffito M: The clinical pharmacology of antiretrovirals in development. Expert Opin Drug Metab Toxicol. 2006 Jun;2(3):447-58. [Article]
6. O'Neal R: MK-0518 and GS-9137: two promising integrase inhibitors in the pipeline. BETA. 2006 Summer;18(4):13-6. [Article]
7. James JS: Integrase inhibitor MK-0518: Merck opens expanded-access program. AIDS Treat News. 2006 Jul-Sep;(419):5. [Article]
8. Markowitz M, Morales-Ramirez JO, Nguyen BY, Kovacs CM, Steigbigel RT, Cooper DA, Liporace R, Schwartz R, Isaacs R, Gilde LR, Wenning L, Zhao J, Teppler H: Antiretroviral activity, pharmacokinetics, and tolerability of MK-0518, a novel inhibitor of HIV-1 integrase, dosed as monotherapy for 10 days in treatment-naive HIV-1-infected individuals. J Acquir Immune Defic Syndr. 2006 Dec 15;43(5):509-15. [Article]
9. Colquitt AR, Pham PA: Expanded access drug profile: raltegravir (RAL, MK-0518). Hopkins HIV Rep. 2007 Jan;19(1):11-2. [Article]
10. Authors unspecified: Raltegravir demonstrates potency. AIDS Patient Care STDS. 2007 Apr;21(4):288. [Article]
11. Authors unspecified: Anti-HIV agents. Raltegravir--other issues. TreatmentUpdate. 2007 Feb;19(2):9-10. [Article]
12. Authors unspecified: Anti-HIV agents. Integrase inhibitor raltegravir makes its mark. TreatmentUpdate. 2007 Feb;19(2):8-9. [Article]
13. Cahn P, Sued O: Raltegravir: a new antiretroviral class for salvage therapy. Lancet. 2007 Apr 14;369(9569):1235-6. [Article]
14. FDA Approved Drug Products: ISENTRESS (raltegravir) oral suspension and tablets [Link]

External Links

KEGG Drug

D06676

PubChem Compound

54671008

PubChem Substance

175427095

ChemSpider

16445111

BindingDB

25351

RxNav

719872

ChEBI

82960

ChEMBL

CHEMBL254316

ZINC

ZINC000013831130

PDBe Ligand

RLT

Drugs.com

Drugs.com Drug Page

Wikipedia

Raltegravir

PDB Entries

3l2v / 4mda / 4mdb / 7lw6 / 7m0n / 7oug

FDA label

Download (127 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)	1
4	Completed	Basic Science	Hepatitis C Virus (HCV) Infection / Human Immunodeficiency Virus (HIV) Infections	1
4	Completed	Health Services Research	Human Immunodeficiency Virus (HIV) Infections	1
4	Completed	Prevention	Human Immunodeficiency Virus (HIV) Infections	6
4	Completed	Screening	Fatty Liver / Human Immunodeficiency Virus (HIV) Infections / Non Alcoholic Steatohepatitis (NASH)	1

Pharmacoeconomics

Manufacturers

Not Available

Packagers

Not Available

Dosage Forms

Form	Route	Strength
Tablet, film coated	Oral
Granule, for suspension	Oral	100 MG
Granule, for suspension	Oral	100 mg/1
Tablet	Oral	100 MG
Tablet	Oral	25 MG
Tablet	Oral	400 mg
Tablet, chewable	Oral	100 mg/1
Tablet, chewable	Oral	100 mg
Tablet, chewable	Oral	25 mg
Tablet, chewable	Oral	25 mg/1
Tablet, film coated	Oral	400 mg/1
Tablet, film coated	Oral	600 mg/1
Tablet, film coated	Oral
Tablet, film coated	Oral	600 mg
Tablet, film coated	Oral	400 mg
Tablet	Oral	600 mg
Granule	Oral	100 mg
Powder	Not applicable	1 kg/1kg
Tablet, coated	Oral	400 mg

Prices

Not Available

Patents

Patent Number	Pediatric Extension	Approved	Expires (estimated)	Region
US7217713	Yes	2007-05-15	2023-04-21
US7435734	Yes	2008-10-14	2023-04-21
US7754731	Yes	2010-07-13	2029-09-11
US7169780	Yes	2007-01-30	2024-04-03
US7820660	No	2010-10-26	2023-04-25
US9649311	Yes	2017-05-16	2031-04-21
US10772888	No	2020-09-15	2032-03-30
US8771733	No	2014-07-08	2030-06-02
US8852632	No	2014-10-07	2028-01-28

Properties

State

Solid

Experimental Properties

Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.0976 mg/mL	ALOGPS
logP	1.3	ALOGPS
logP	-0.39	Chemaxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	7.02	Chemaxon
pKa (Strongest Basic)	-1.1	Chemaxon
Physiological Charge	-1	Chemaxon
Hydrogen Acceptor Count	7	Chemaxon
Hydrogen Donor Count	3	Chemaxon
Polar Surface Area	150.02 Å2	Chemaxon
Rotatable Bond Count	6	Chemaxon
Refractivity	112.59 m3·mol-1	Chemaxon
Polarizability	42.45 Å3	Chemaxon
Number of Rings	3	Chemaxon
Bioavailability	1	Chemaxon
Rule of Five	Yes	Chemaxon
Ghose Filter	Yes	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
LC-MS/MS Spectrum - LC-ESI-qTof , Positive	LC-MS/MS	splash10-014i-0011900000-1f750fd89ed368c2519a
MS/MS Spectrum - , positive	LC-MS/MS	splash10-01ot-0417900000-7f0f52f17ac409473482
MS/MS Spectrum - , positive	LC-MS/MS	splash10-014i-0011900000-1f750fd89ed368c2519a
Predicted MS/MS Spectrum - 10V, Positive (Annotated)	Predicted LC-MS/MS	splash10-00dj-0009500000-26a8f54d48aea57707b8
Predicted MS/MS Spectrum - 10V, Negative (Annotated)	Predicted LC-MS/MS	splash10-006x-6319500000-fe3f71303a26392c077b
Predicted MS/MS Spectrum - 20V, Positive (Annotated)	Predicted LC-MS/MS	splash10-00dl-0229300000-95c9dc1735afbf3cf0b6
Predicted MS/MS Spectrum - 20V, Negative (Annotated)	Predicted LC-MS/MS	splash10-0g4i-6669300000-d4ebb4258b1464c03b23
Predicted MS/MS Spectrum - 40V, Positive (Annotated)	Predicted LC-MS/MS	splash10-0kmj-1689200000-15f416664f9ac6251029
Predicted MS/MS Spectrum - 40V, Negative (Annotated)	Predicted LC-MS/MS	splash10-00l6-9411100000-9cbafc2e930d4a578762
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]-	202.82045	predicted	DeepCCS 1.0 (2019)
[M+H]+	205.21602	predicted	DeepCCS 1.0 (2019)
[M+Na]+	211.16913	predicted	DeepCCS 1.0 (2019)

Targets

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Details1. Integrase

Kind

Protein

Organism

Human immunodeficiency virus 1

Pharmacological action

Yes

Actions

Inhibitor

General Function

Zinc ion binding

Specific Function

Not Available

Gene Name

pol

Uniprot ID

Q7ZJM1

Uniprot Name

Integrase

Molecular Weight

32226.645 Da

References

1. Evering TH, Markowitz M: Raltegravir: an integrase inhibitor for HIV-1. Expert Opin Investig Drugs. 2008 Mar;17(3):413-22. doi: 10.1517/13543784.17.3.413 . [Article]
2. Anker M, Corales RB: Raltegravir (MK-0518): a novel integrase inhibitor for the treatment of HIV infection. Expert Opin Investig Drugs. 2008 Jan;17(1):97-103. [Article]

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Drug created at September 14, 2010 16:21 / Updated at February 20, 2024 23:54