Raltegravir

Identification

Name

Raltegravir

Accession Number

DB06817

Description

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

Pharmacology

Indication

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

Associated Conditions

• Human Immunodeficiency Virus Type 1 (HIV-1) Infection

Associated Therapies

• Post-exposure prophylaxis for occupational exposure to HIV therapy

Contraindications & Blackbox Warnings

Learn about our commercial Contraindications & Blackbox Warnings data.

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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

Learn about our commercial Adverse Effects data.

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Toxicity

Not Available

Affected organisms

• Human Immunodeficiency Virus

Pathways

Not Available

Pharmacogenomic Effects/ADRs

Not Available

Interactions

Drug Interactions

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.
Aluminium	The serum concentration of Raltegravir can be decreased when it is combined with Aluminium.
Aluminium phosphate	The serum concentration of Raltegravir can be decreased when it is combined with Aluminium phosphate.
Aluminum chloride	Aluminum chloride can cause a decrease in the absorption of Raltegravir resulting in a reduced serum concentration and potentially a decrease in efficacy.
Aluminum hydroxide	The serum concentration of Raltegravir can be decreased when it is combined with Aluminum hydroxide.
Aluminum sulfate	Aluminum sulfate can cause a decrease in the absorption of Raltegravir resulting in a reduced serum concentration and potentially a decrease in efficacy.

Additional Data Available

Extended Description
Extended Description
Extended description of the mechanism of action and particular properties of each drug interaction.
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Severity
Severity
A severity rating for each drug interaction, from minor to major.
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Evidence Level
Evidence Level
A rating for the strength of the evidence supporting each drug interaction.
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Action
Action
An effect category for each drug interaction. Know how this interaction affects the subject drug.
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Food Interactions

• Take with or without food.

Products

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
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Isentress	Tablet, chewable	100 mg/1	Oral	Merck Sharp & Dohme Corp.	2011-12-21	Not applicable
Isentress	Tablet, film coated	400 mg/1	Oral	REMEDYREPACK INC.	2018-10-31	Not applicable
Isentress	Tablet	400 mg	Oral	Merck Ltd.	2007-11-28	Not applicable
Isentress	Tablet, film coated	400 mg/1	Oral	State of Florida DOH Central Pharmacy	2009-07-01	Not applicable
Isentress	Tablet, film coated	400 mg/1	Oral	H.J. Harkins Company	2017-07-31	Not applicable
Isentress	Granule, for suspension	100 mg/1	Oral	Merck Sharp & Dohme Corp.	2013-12-20	Not applicable
Isentress	Tablet, film coated	400 mg/1	Oral	RedPharm Drug, Inc.	2007-10-12	Not applicable
Isentress	Tablet, chewable	100 mg	Oral	Merck Ltd.	2013-02-11	Not applicable
Isentress	Tablet, film coated	400 mg/1	Oral	Dispensing Solutions, Inc.	2007-10-12	Not applicable
Isentress	Tablet, film coated	400 mg/1	Oral	Merck Sharp & Dohme Corp.	2007-10-12	Not applicable

Additional Data Available

Application Number
Application Number
A unique ID assigned by the FDA when a product is submitted for approval by the labeller.
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Product Code
Product Code
A governmentally-recognized ID which uniquely identifies the product within its regulatory market.
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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

J05AX08 — Raltegravir

• J05AX — Other antivirals
• 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
• 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)

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. [PubMed:24145879]
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. [PubMed:23856784]
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. [PubMed:23836466]
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. [PubMed:23664333]
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. [PubMed:16863445]
6. O'Neal R: MK-0518 and GS-9137: two promising integrase inhibitors in the pipeline. BETA. 2006 Summer;18(4):13-6. [PubMed:17019786]
7. James JS: Integrase inhibitor MK-0518: Merck opens expanded-access program. AIDS Treat News. 2006 Jul-Sep;(419):5. [PubMed:17096488]
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. [PubMed:17133211]
9. Colquitt AR, Pham PA: Expanded access drug profile: raltegravir (RAL, MK-0518). Hopkins HIV Rep. 2007 Jan;19(1):11-2. [PubMed:17569171]
10. Authors unspecified: Raltegravir demonstrates potency. AIDS Patient Care STDS. 2007 Apr;21(4):288. [PubMed:17506141]
11. Authors unspecified: Anti-HIV agents. Raltegravir--other issues. TreatmentUpdate. 2007 Feb;19(2):9-10. [PubMed:17447317]
12. Authors unspecified: Anti-HIV agents. Integrase inhibitor raltegravir makes its mark. TreatmentUpdate. 2007 Feb;19(2):8-9. [PubMed:17447316]
13. Cahn P, Sued O: Raltegravir: a new antiretroviral class for salvage therapy. Lancet. 2007 Apr 14;369(9569):1235-6. [PubMed:17434380]

External Links

KEGG Drug

D06676

PubChem Compound

54671008

PubChem Substance

175427095

ChemSpider

16445111

BindingDB

25351

RxNav

719872

ChEMBL

CHEMBL254316

ZINC

ZINC000013831130

PDBe Ligand

RLT

Drugs.com

Drugs.com Drug Page

Wikipedia

Raltegravir

AHFS Codes

• 08:18.08.12 — HIV Integrase Inhibitors

PDB Entries

3l2v / 3oya / 4mda / 4mdb

FDA label

Download (127 KB)

Clinical Trials

Clinical Trials

Phase	Status	Purpose	Conditions	Count
4	Completed	Not Available	Healthy Volunteers	1
4	Completed	Basic Science	Hepatitis C Viral 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	5
4	Completed	Treatment	Adverse Drug Reaction (ADR) / Human Immunodeficiency Virus (HIV) Infections / Quality of Life	1
4	Completed	Treatment	Aging-related Inflammation in HIV-infected Patients	1
4	Completed	Treatment	Cardiovascular Heart Disease / Human Immunodeficiency Virus (HIV) Infections	1
4	Completed	Treatment	Cardiovascular Heart Disease / Human Immunodeficiency Virus (HIV) Infections / Inflammatory Reaction	1
4	Completed	Treatment	Fatty Liver / HIV Seropositivity / Metabolic Syndromes	1
4	Completed	Treatment	HCV Coinfection / Human Immunodeficiency Virus (HIV) Infections	1

Pharmacoeconomics

Manufacturers

Not Available

Packagers

Not Available

Dosage Forms

Form	Route	Strength
Tablet, film coated	Oral
Tablet, film coated	Oral	150 MG
Granule, for suspension	Oral	100 mg/1
Granule, for suspension	Oral	100 MG
Tablet	Oral	100 MG
Tablet	Oral	25 MG
Tablet	Oral	400 mg
Tablet, chewable	Oral	100 mg/1
Tablet, chewable	Oral	25 mg/1
Tablet, coated	Oral	400 mg
Tablet, film coated	Oral	400 MG
Tablet, film coated	Oral	400 mg/1
Tablet, film coated	Oral	600 MG
Tablet, film coated	Oral	600 mg/1
Tablet, coated		400 mg
Tablet
Tablet	Oral
Tablet	Oral	600 mg
Granule	Oral	100 mg
Tablet, chewable	Oral	100 mg
Tablet, chewable	Oral	25 mg
Powder	Not applicable	1 kg/1kg

Prices

Not Available

Patents

Patent Number	Pediatric Extension	Approved	Expires (estimated)	Region
Unlock Additional Data
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

Additional Data Available

Filed On
Filed On
The date on which a patent was filed with the relevant government.
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Properties

State

Solid

Experimental Properties

Not Available

Predicted Properties

Property	Value	Source
logP	-0.39	ChemAxon
pKa (Strongest Acidic)	5.62	ChemAxon
pKa (Strongest Basic)	-1.5	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	42.47 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
Predicted MS/MS Spectrum - 10V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
LC-MS/MS Spectrum - LC-ESI-qTof , Positive	LC-MS/MS	Not Available
MS/MS Spectrum - , positive	LC-MS/MS	splash10-01ot-0417900000-7f0f52f17ac409473482
MS/MS Spectrum - , positive	LC-MS/MS	splash10-014i-0011900000-1f750fd89ed368c2519a

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Drug created on September 14, 2010 10:21 / Updated on October 25, 2020 09:16