Maraviroc

Maraviroc
Clinical data
Pronunciation	/məˈrævɪrɒk/ mə-RAV-i-rok Selzentry: /sɛlˈzɛntri/
Trade names	Selzentry, Celsentri
Other names	UK-427857, 4,4-Difluoro-N-[(1S)-3-{(1R,3s,5S)-3-[3-methyl-5-(propan-2-yl)-4H-1,2,4-triazol-4-yl]-8-azabicyclo[3.2.1]octan-8-yl}-1-phenylpropyl]; cyclohexanecarboxamide
AHFS/Drugs.com	Monograph
MedlinePlus	a607076
License data	US DailyMed: Maraviroc;
Pregnancy; category	AU: B1;
Routes of; administration	By mouth
ATC code	J05AX09 (WHO) ;
Legal status
Legal status	AU: S4 (Prescription only); UK: POM (Prescription only); US: ℞-only; EU: Rx-only;
Pharmacokinetic data
Bioavailability	23%
Protein binding	~76%
Metabolism	Liver (CYP, predominantly CYP3A)
Metabolites	Secondary amine formed by N-dealkylation (major)
Elimination half-life	14–18 hours (mean 16 hours)
Excretion	Feces (76%), urine (20%)
Identifiers
	IUPAC name 4,4-Difluoro-N-{(1S)-3-[3-(3-isopropyl- 5-methyl-4H-1,2,4-triazol-4-yl)-8-azabicyclo[3.2.1]oct-8-yl]-1-phenylpropyl}cyclohexanecarboxamide;
CAS Number	376348-65-1 ;
PubChem CID	3002977;
IUPHAR/BPS	806;
DrugBank	DB04835 ;
ChemSpider	20078004 ;
UNII	MD6P741W8A;
ChEBI	CHEBI:63608 ;
ChEMBL	ChEMBL1201187 ;
NIAID ChemDB	104834;
CompTox Dashboard (EPA)	DTXSID8048949 ;
ECHA InfoCard	100.124.927
Chemical and physical data
Formula	C29H41F2N5O
Molar mass	513.678 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES Cc5nnc(n5[C@@H]1C[C@H]4CC[C@@H](C1)N4CC[C@H](NC(=O)C2CCC(F)(F)CC2)c3ccccc3)C(C)C;
	InChI InChI=1S/C29H41F2N5O/c1-19(2)27-34-33-20(3)36(27)25-17-23-9-10-24(18-25)35(23)16-13-26(21-7-5-4-6-8-21)32-28(37)22-11-14-29(30,31)15-12-22/h4-8,19,22-26H,9-18H2,1-3H3,(H,32,37)/t23-,24+,25-,26-/m0/s1 ; Key:GSNHKUDZZFZSJB-QYOOZWMWSA-N ;
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Maraviroc, sold under the brand names Selzentry (US) and Celsentri (EU), is an antiretroviral medication used to treat HIV infection. It is taken by mouth. It is in the CCR5 receptor antagonist class.

It was approved for medical use in the United States in August 2007, and in the European Union in September 2007.

Clinical data


Pronunciation	/məˈrævɪrɒk/ mə-RAV-i-rok Selzentry: /sɛlˈzɛntri/
Trade names	Selzentry, Celsentri
Other names	UK-427857, 4,4-Difluoro-N-[(1S)-3-{(1R,3s,5S)-3-[3-methyl-5-(propan-2-yl)-4H-1,2,4-triazol-4-yl]-8-azabicyclo[3.2.1]octan-8-yl}-1-phenylpropyl] cyclohexanecarboxamide
AHFS/Drugs.com	Monograph
MedlinePlus	a607076
License data	US DailyMed: Maraviroc
Pregnancy category	AU: B1
Routes of administration	By mouth
ATC code	J05AX09 (WHO)
Legal status
Legal status	AU: S4 (Prescription only) UK: POM (Prescription only) US: ℞-only EU: Rx-only
Pharmacokinetic data
Bioavailability	23%
Protein binding	~76%
Metabolism	Liver (CYP, predominantly CYP3A)
Metabolites	Secondary amine formed by N-dealkylation (major)
Elimination half-life	14–18 hours (mean 16 hours)
Excretion	Feces (76%), urine (20%)
Identifiers
IUPAC name 4,4-Difluoro-N-{(1S)-3-[3-(3-isopropyl- 5-methyl-4H-1,2,4-triazol-4-yl)-8-azabicyclo[3.2.1]oct-8-yl]-1-phenylpropyl}cyclohexanecarboxamide
CAS Number	376348-65-1^Y
PubChem CID	3002977
IUPHAR/BPS	806
DrugBank	DB04835^Y
ChemSpider	20078004^N
UNII	MD6P741W8A
ChEBI	CHEBI:63608^N
ChEMBL	ChEMBL1201187^N
NIAID ChemDB	104834
CompTox Dashboard (EPA)	DTXSID8048949
ECHA InfoCard	100.124.927
Chemical and physical data
Formula	C₂₉H₄₁F₂N₅O
Molar mass	513.678 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES Cc5nnc(n5[C@@H]1C[C@H]4CC[C@@H](C1)N4CC[C@H](NC(=O)C2CCC(F)(F)CC2)c3ccccc3)C(C)C
InChI InChI=1S/C29H41F2N5O/c1-19(2)27-34-33-20(3)36(27)25-17-23-9-10-24(18-25)35(23)16-13-26(21-7-5-4-6-8-21)32-28(37)22-11-14-29(30,31)15-12-22/h4-8,19,22-26H,9-18H2,1-3H3,(H,32,37)/t23-,24+,25-,26-/m0/s1^N Key:GSNHKUDZZFZSJB-QYOOZWMWSA-N^N
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