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Cobicistat

CAS No.
1004316-88-4
Chemical Name:
Cobicistat
Synonyms
Tybost;Cobicistat (GS-9350);GS9350;CS-753;GS-9350;GS 9350;Genvoya.;Cobicistat;Cobiclstat;Cobicistat D8
CBNumber:
CB62627692
Molecular Formula:
C40H53N7O5S2
Molecular Weight:
776.02
MDL Number:
MFCD18251449
MOL File:
1004316-88-4.mol
Last updated:2023-05-18 11:31:04

Cobicistat Properties

Melting point 50-54°C
Boiling point 974.5±65.0 °C(Predicted)
Density 1.228±0.06 g/cm3 (20 ºC 760 Torr)
storage temp. Hygroscopic, Refrigerator, under inert atmosphere
solubility Chloroform (Slightly), DMSO (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly)
form Solid
pka 11.86±0.46(Predicted)
color White to Off-White
Stability Hygroscopic
InChIKey ZCIGNRJZKPOIKD-CQXVEOKZSA-N
SMILES C(OCC1SC=NC=1)(=O)N[C@@H](CC1=CC=CC=C1)CC[C@H](CC1=CC=CC=C1)NC(=O)[C@H](CCN1CCOCC1)NC(=O)N(C)CC1=CSC(C(C)C)=N1
FDA UNII LW2E03M5PG
ATC code V03AX03

Pharmacokinetic data

Protein binding 97-98%
Excreted unchanged in urine 8.2%
Biological half-life 3-4

Cobicistat price More Price(34)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Cayman Chemical 23433 Cobicistat ≥98% 1004316-88-4 1mg $37 2024-03-01 Buy
Cayman Chemical 23433 Cobicistat ≥98% 1004316-88-4 5mg $151 2024-03-01 Buy
Cayman Chemical 26442 Cobicistat-d8 ≥99% deuterated forms (d1-d8) 1004316-88-4 1mg $922 2023-01-06 Buy
Cayman Chemical 23433 Cobicistat ≥98% 1004316-88-4 10mg $266 2024-03-01 Buy
Cayman Chemical 23433 Cobicistat ≥98% 1004316-88-4 25mg $573 2024-03-01 Buy
Product number Packaging Price Buy
23433 1mg $37 Buy
23433 5mg $151 Buy
26442 1mg $922 Buy
23433 10mg $266 Buy
23433 25mg $573 Buy

Cobicistat Chemical Properties,Uses,Production

Description

Cobicistat (GS-9350) is a potent and selective inhibitor of CYP3A with IC50 of 30-285 nM.

In vitro

Cobicistat (GS-9350) is a potent, and selective inhibitor of human cytochrome P450 3A (CYP3A) enzymes as a pharmacoenhancer. GS-9350 inhibits CYP3A with IC50 spectrum from 30 nM to 285 nM. In contrast to ritonavir, GS-9350 is devoid of anti-HIV activity, with IC50 of > 30μM against HIV-1 protease and EC50 of > 30μM in MT-2 HIV infection assay, and is thus more suitable for use in boosting anti-HIV drugs without risking selection of potential drug-resistant HIV variants. GS-9350 shows reduced liability for drug interactions and may have potential improvements in tolerability over ritonavir.

Description

Cobicistat, a selective, mechanism-based CYP3A inhibitor, was discovered and developed by Gilead Sciences, Inc. In 2013, European Medicines Agency (EMA) approved cobicistat (Tybost) for the treatment of HIV-1 infection in combination with protease inhibitors (PIs) atazanavir or darunavir. Interestingly, cobicistat does not interact with HIV directly, but instead serves as a pharmacokinetic enhancer to boost the anti-HIV effect of atazanavir or darunavir through blockade of CYP3A. Cobicistat slows CYP-mediated metabolism of atazanavir and darunavir, resulting in prolonged systemic exposure of the drug(s). Cobicistat is also available as part of a fixed-dose combination tablet (Stribild) of four additional drugs with CYP3A liabilities (elvitegravir, cobicistat, emtricitabine and tenofovir disoproxil fumarate), which was approved in U.S. in 2012, and subsequently approved in Europe and Japan in 2013.

Originator

Gilead (United States)

Uses

Antiretroviral;Labeled Cobicistat, intended for use as an internal standard for the quantification of Cobicistat by GC- or LC-mass spectrometry.

Uses

Isotope labelled analogue of Cobicistat (C633150), a HIV protease inhibitor and have been coadministered with low-dose ritonavir (R535000) as a pharmacoenhancer, significantly increasing their plasma concentrations.

Uses

Cobicistat is a HIV protease inhibitor and have been coadministered with low-dose ritonavir (R535000) as a pharmacoenhancer, significantly increasing their plasma concentrations.

Definition

ChEBI: Cobicistat is a monocarboxylic acid amide obtained by formal condensation of the carboxy group of (2S)-2-({[(2-isopropyl-1,3-thiazol-4-yl)methyl](methyl)carbamoyl}amino)-4-(morpholin-4-yl)butanoic acid with the amino group of 1,3-thiazol-5-ylmethyl [(2R,5R)-5-amino-1,6-diphenylhexan-2-yl]carbamate. Acts as a pharmacoenhancer in treatment of HIV-1 by inhibiting P450 enzymes that metabolise other medications.. It has a role as a P450 inhibitor. It is a member of 1,3-thiazoles, a member of morpholines, a member of ureas, a carbamate ester and a monocarboxylic acid amide.

brand name

Tybost

Clinical Use

Pharmacokinetic enhancer used to increase the effect of atazanavir and darunavir

Synthesis

Commercial L-methionine (24) was treated with bromoacetic acid at elevated temperatures to afford aminolactone salt 25 in 70% yield. This material was then reacted with methyl aminomethylthiazole (26) in the presence of CDI and diisopropylethylamine to arrive at urea 27 in 91% yield. Next, lactone 27 underwent a ring-opening sequence upon exposure to trimethylsilyl iodide (TMSI) giving intermediate 28. The iodide was then displaced by morpholine, followed by treatment with oxalic acid to deliver the L-thiazole morpholine ethyl ester as the oxalate salt 29 in 71% yield for the sequence. Base-mediated hydrolysis of ethyl ester 29, followed by treatment of carboxylate 30 with mono-carbonate hydrochloride 31 in the presence of EDCI and HOBT, provided cobicistat (V) in 76% yield for two steps.

Synthesis_1004316-88-4

Drug interactions

Potentially hazardous interactions with other drugsAlpha-blockers: concentration of alfuzosin possibly increased - avoid.
Anti-arrhythmics: concentration of amiodarone possibly increased - avoid.
Antibacterials: concentration reduced by rifabutin and rifampicin - adjust cobicistat dose, avoid with rifampicin.
Anticoagulants: avoid with apixaban; anticoagulant effect of rivaroxaban possibly enhanced - avoid.
Antidepressants: concentration possibly reduced by St John’s wort - avoid.
Antiepileptics: concentration of cobicistat possibly reduced by carbamazepine, fosphenytoin phenobarbital, phenytoin and primidone - avoid.
Antifungals: concentration of itraconazole and ketoconazole possibly increased - reduce antifungal dose.
Antipsychotics: concentration of lurasidone and pimozide possibly increased - avoid.
Antivirals: concentration of daclatasvir and maraviroc possibly increased - reduce daclatasvir and maraviroc dose; avoid with dasabuvir, nevirapine, ombitasvir, paritaprevir, ritonavir and simeprevir; concentration of elbasvir and grazoprevir increased - avoid; concentration of olaparib possibly increased - avoid or reduce olaparib dose; concentration of both drugs reduced with tipranavir - avoid.
Anxiolytics: avoid with oral midazolam.
Avanafil: concentration of avanafil possibly increased - avoid.
Bosentan: avoid concomitant use.
Cardiac glycosides: concentration of digoxin possibly increased - reduce initial dose of digoxin.
Corticosteroids: concentration of corticosteroids possibly increased avoid or use with caution.
Cytotoxics: concentration of ibrutinib possibly increased - reduce ibrutinib dose; concentration of olaparib possibly increased - avoid or reduce dose of olaparib.
Domperidone: possible increased risk of ventricular arrhythmias - avoid.
Ergot alkaloids: concentration of ergot alkaloids possibly increased - avoid.
Immunosuppression: concentration of ciclosporin, sirolimus and tacrolimus possibly increased.
Lipid-lowering drugs: concentration of atorvastatin possibly increased - reduce atorvastatin dose; avoid with simvastatin.
Oestrogens: metabolism of oestrogens accelerated, reduced contraceptive effect - avoid or use with caution.
Salmeterol: avoid concomitant use. Sildenafil: concentration of sildenafil possibly increased - avoid sildenafil for pulmonary arterial hypertension, reduce dose for erectile dysfunction.
Tadalafil: concentration of tadalafil possibly increased - reduce dose of tadalafil.
Vardenafil: concentration of vardenafil possibly increased - reduce dose of vardenafil.

Metabolism

Cobicistat is metabolised via CYP3A (major)- and CYP2D6 (minor)-mediated oxidation. Following oral administration of [14C]-cobicistat, 99% of circulating radioactivity in plasma was unchanged cobicistat. Low levels of metabolites are observed in urine and faeces and do not contribute to the CYP3A inhibitory activity of cobicistat.
Following oral administration of [14C]-cobicistat, 86% and 8.2% of the dose were recovered in faeces and urine, respectively.

References

[1] deeks ed. cobicistat: a review of its use as a pharmacokinetic enhancer of atazanavir and darunavir in patients with hiv-1 infection. drugs. 2014 feb;74(2):195-206.

Cobicistat Preparation Products And Raw materials

Raw materials

Preparation Products

Global( 188)Suppliers
Supplier Tel Email Country ProdList Advantage
Hangzhou Benoy Chemical Co., Ltd
+8617342059697 sales@benoychem.com China 315 58
Alpha Biopharmaceuticals Co., Ltd
+86-15542445688 sales@alabiochem.com China 888 58
Beijing Cooperate Pharmaceutical Co.,Ltd
010-60279497 sales01@cooperate-pharm.com CHINA 1811 55
Henan Tianfu Chemical Co.,Ltd.
+86-0371-55170693 +86-19937530512 info@tianfuchem.com China 21667 55
career henan chemical co
+86-0371-86658258 +8613203830695 sales@coreychem.com China 29888 58
SHANDONG ZHI SHANG CHEMICAL CO.LTD
+86 18953170293 sales@sdzschem.com China 2931 58
Biochempartner
0086-13720134139 candy@biochempartner.com CHINA 967 58
Hubei Jusheng Technology Co.,Ltd.
18871490254 linda@hubeijusheng.com CHINA 28180 58
Changzhou PBpharmaceutical R&D Co.,Ltd
0519-83990708 info@pbpharm.com CHINA 498 58
BOC Sciences
+1-631-485-4226 inquiry@bocsci.com United States 19553 58

View Lastest Price from Cobicistat manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
Cobicistat pictures 2024-08-30 Cobicistat
1004316-88-4
US $2063.00 / g 1g 99 1kg Baoji Guokang Bio-Technology Co., Ltd.
Cobicistat pictures 2022-10-14 Cobicistat
1004316-88-4
US $0.00-0.00 / KG 1KG 98% 1Ton Henan Aochuang Chemical Co.,Ltd.
Cobicistat pictures 2021-07-13 Cobicistat
1004316-88-4
US $15.00-10.00 / KG 1KG 99%+ HPLC Monthly supply of 1 ton Zhuozhou Wenxi import and Export Co., Ltd
  • Cobicistat pictures
  • Cobicistat
    1004316-88-4
  • US $2063.00 / g
  • 99
  • Baoji Guokang Bio-Technology Co., Ltd.
  • Cobicistat pictures
  • Cobicistat
    1004316-88-4
  • US $0.00-0.00 / KG
  • 98%
  • Henan Aochuang Chemical Co.,Ltd.
  • Cobicistat pictures
  • Cobicistat
    1004316-88-4
  • US $15.00-10.00 / KG
  • 99%+ HPLC
  • Zhuozhou Wenxi import and Export Co., Ltd

Cobicistat Spectrum

(3R,6R,9S)-12-Methyl-13-[2-(1-methylethyl)-4-thiazolyl]-9-[2-(4-morpholinyl)ethyl]-8,11-dioxo-3,6-bis(phenylmethyl)-2,7,10,12-tetraazatridecanoic acid 5-thiazolylmethyl ester Cobicistat thiazol-5-ylMethyl (2R,5R)-5-((S)-2-(3-((2-isopropylthiazol-4-yl)Methyl)-3-Methylureido)-4-MorpholinobutanaMido)-1,6-diphenylhexan-2-ylcarbaMate GS 9350 GS9350 GS-9350 Cobicistat D8 2,7,10,12-Tetraazatridecanoic acid, 12-Methyl-13-[2-(1-Methylethyl)-4-thiazolyl]-9-[2-(4-Morpholinyl)ethyl]-8,11-dioxo-3,6-bis(phenylMethyl)-, 5-thiazolylMethyl ester, (3R,6R,9S)- Cobiclstat Thiazol-5-ylmethyl (2R,5R)-5-((S)-2-(3-((2-isopropylthiazol-4-yl)methyl)-3-methylureido)-4-mor Cobicistat, brand name: Tybost Genvoya. GS9350; GS-9350; GS 9350; COBICISTAT, BRAND NAME: TYBOST; GENVOYA. CS-753 GS 9350; GS9350 COBICISTAT 1004316-88-4 Cobicistat USP/EP/BP 1,3-thiazol-5-ylmethyl N-[(2r,5r)-5-[[(2s)-2-[[methyl-[(2-propan-2-yl-1,3-thiazol-4-yl)methyl]carbamoyl]amino]-4-morpholin-4-ylbutanoyl]amino]-1,6-diphenylhexan-2-yl]carbamate Cobicistat (10mM in DMSO) CobicistatQ: What is Cobicistat Q: What is the CAS Number of Cobicistat Q: What is the storage condition of Cobicistat Q: What are the applications of Cobicistat Cobicistat D8Q: What is Cobicistat D8 Q: What is the CAS Number of Cobicistat D8 Q: What is the storage condition of Cobicistat D8 Q: What are the applications of Cobicistat D8 C40H53N7O5S2 Cobicistat 1004316-88-4 Tybost Cobicistat (GS-9350) 1004316-88-4 C40H53N7O5S2 Inhibitors Inhibitor