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	EU EMA: by INN; US FDA: Maraviroc;
Pregnancy; category	AU: B1; ;
Routes of; administration	By mouth
ATC code	J05AX09 (WHO) ;
Legal status
Legal status	UK: POM (Prescription only); US: WARNINGRx-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.^[2]^[3] It is taken by mouth.^[2]^[3] It is in the CCR5 receptor antagonist class.^[2]^[3]

It was approved for medical use in the United States in August 2007,^[2] and in the European Union in September 2007.^[3]

^ "FDA-sourced list of all drugs with black box warnings (Use Download Full Results and View Query links.)". nctr-crs.fda.gov. FDA. Retrieved 22 October 2023.
^ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ "Selzentry- maraviroc tablet, film coated Selzentry- maraviroc solution". DailyMed. 18 July 2018. Retrieved 31 July 2020.
^ ^a ^b ^c ^d ^e "Celsentri EPAR". European Medicines Agency (EMA). 17 September 2018. Retrieved 31 July 2020.
^ Abel S, Russell D, Whitlock LA, Ridgway CE, Nedderman AN, Walker DK (April 2008). "Assessment of the absorption, metabolism and absolute bioavailability of maraviroc in healthy male subjects". British Journal of Clinical Pharmacology. 65 (Suppl 1): 60–7. doi:10.1111/j.1365-2125.2008.03137.x. PMC 2311408. PMID 18333867.
^ Abel S, Back DJ, Vourvahis M (2009). "Maraviroc: pharmacokinetics and drug interactions". Antiviral Therapy. 14 (5): 607–18. doi:10.1177/135965350901400514. PMID 19704163. S2CID 29064286.

[FDA-AllBoxedWarnings-1] "FDA-sourced list of all drugs with black box warnings (Use Download Full Results and View Query links.)". nctr-crs.fda.gov. FDA. Retrieved 22 October 2023.

[Selzentry_FDA_label-2] ^ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ "Selzentry- maraviroc tablet, film coated Selzentry- maraviroc solution". DailyMed. 18 July 2018. Retrieved 31 July 2020.

[Celsentri_EPAR-3] "Celsentri EPAR". European Medicines Agency (EMA). 17 September 2018. Retrieved 31 July 2020.

[4] Abel S, Russell D, Whitlock LA, Ridgway CE, Nedderman AN, Walker DK (April 2008). "Assessment of the absorption, metabolism and absolute bioavailability of maraviroc in healthy male subjects". British Journal of Clinical Pharmacology. 65 (Suppl 1): 60–7. doi:10.1111/j.1365-2125.2008.03137.x. PMC 2311408. PMID 18333867.

[5] Abel S, Back DJ, Vourvahis M (2009). "Maraviroc: pharmacokinetics and drug interactions". Antiviral Therapy. 14 (5): 607–18. doi:10.1177/135965350901400514. PMID 19704163. S2CID 29064286.

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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	EU EMA: by INN US FDA: Maraviroc
Pregnancy category	AU: B1
Routes of administration	By mouth
ATC code	J05AX09 (WHO)
Legal status
Legal status	UK: POM (Prescription only) US: WARNING^[1]Rx-only^[2] EU: Rx-only^[3]
Pharmacokinetic data
Bioavailability	23%^[4]
Protein binding	~76%^[2]
Metabolism	Liver (CYP, predominantly CYP3A)^[2]
Metabolites	Secondary amine formed by N-dealkylation (major)
Elimination half-life	14–18 hours^[2] (mean 16 hours)^[5]
Excretion	Feces (76%), urine (20%)^[2]
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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