Cabotegravir
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MedKoo CAT#: 319641

CAS#: 1051375-10-0

Description: Cabotegravir, also known as S/GSK1265744 or GSK744, is potent HIV integrase inhibitor under development for the treatment of HIV infection. Cabotegravir has a carbamoyl pyridone structure similar to dolutegravir.

Chemical Structure

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Cabotegravir
CAS# 1051375-10-0
Instruction

Theoretical Analysis

MedKoo Cat#: 319641
Name: Cabotegravir
CAS#: 1051375-10-0
Chemical Formula: C19H17F2N3O5
Exact Mass: 405.11
Molecular Weight: 405.358
Elemental Analysis: C, 56.30; H, 4.23; F, 9.37; N, 10.37; O, 19.73

Price and Availability

Size Price Availability Quantity
10mg USD 90 Ready to ship
25mg USD 150 Ready to ship
50mg USD 250 Ready to ship
100mg USD 400 Ready to ship
200mg USD 650 Ready to ship
500mg USD 950 Ready to ship
1g USD 1650 Ready to ship
2g USD 2650 Ready to ship
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Related CAS #: 1051375-13-3 (sodium)   1051375-10-0  

Synonym: S/GSK1265744; S/GSK 1265744; S/GSK-1265744; GSK744; GSK-744; GSK 744; Cabotegravir.

IUPAC/Chemical Name: (3S,11aR)-N-(2,4-difluorobenzyl)-6-hydroxy-3-methyl-5,7-dioxo-2,3,5,7,11,11a-hexahydrooxazolo[3,2-a]pyrido[1,2-d]pyrazine-8-carboxamide

InChi Key: WCWSTNLSLKSJPK-LKFCYVNXSA-N

InChi Code: InChI=1S/C19H17F2N3O5/c1-9-8-29-14-7-23-6-12(16(25)17(26)15(23)19(28)24(9)14)18(27)22-5-10-2-3-11(20)4-13(10)21/h2-4,6,9,14,26H,5,7-8H2,1H3,(H,22,27)/t9-,14+/m0/s1

SMILES Code: C[C@H]1CO[C@H]2N1C(C3=C(O)C(C(C(NCC4=C(F)C=C(F)C=C4)=O)=CN3C2)=O)=O

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO, not in water

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 405.36 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
In vitro protocol:
In vivo protocol:

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1: Landovitz RJ, Donnell D, Clement ME, Hanscom B, Cottle L, Coelho L, Cabello R, Chariyalertsak S, Dunne EF, Frank I, Gallardo-Cartagena JA, Gaur AH, Gonzales P, Tran HV, Hinojosa JC, Kallas EG, Kelley CF, Losso MH, Madruga JV, Middelkoop K, Phanuphak N, Santos B, Sued O, Valencia Huamaní J, Overton ET, Swaminathan S, Del Rio C, Gulick RM, Richardson P, Sullivan P, Piwowar-Manning E, Marzinke M, Hendrix C, Li M, Wang Z, Marrazzo J, Daar E, Asmelash A, Brown TT, Anderson P, Eshleman SH, Bryan M, Blanchette C, Lucas J, Psaros C, Safren S, Sugarman J, Scott H, Eron JJ, Fields SD, Sista ND, Gomez-Feliciano K, Jennings A, Kofron RM, Holtz TH, Shin K, Rooney JF, Smith KY, Spreen W, Margolis D, Rinehart A, Adeyeye A, Cohen MS, McCauley M, Grinsztejn B; HPTN 083 Study Team. Cabotegravir for HIV Prevention in Cisgender Men and Transgender Women. N Engl J Med. 2021 Aug 12;385(7):595-608. doi: 10.1056/NEJMoa2101016. PMID: 34379922; PMCID: PMC8448593.


2: Taki E, Soleimani F, Asadi A, Ghahramanpour H, Namvar A, Heidary M. Cabotegravir/Rilpivirine: the last FDA-approved drug to treat HIV. Expert Rev Anti Infect Ther. 2022 Aug;20(8):1135-1147. doi: 10.1080/14787210.2022.2081153. Epub 2022 Jun 13. PMID: 35596583.


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4: Markham A. Cabotegravir Plus Rilpivirine: First Approval. Drugs. 2020 Jun;80(9):915-922. doi: 10.1007/s40265-020-01326-8. PMID: 32495274.


5: Overton ET, Richmond G, Rizzardini G, Jaeger H, Orrell C, Nagimova F, Bredeek F, García Deltoro M, Swindells S, Andrade-Villanueva JF, Wong A, Khuong-Josses MA, Van Solingen-Ristea R, van Eygen V, Crauwels H, Ford S, Talarico C, Benn P, Wang Y, Hudson KJ, Chounta V, Cutrell A, Patel P, Shaefer M, Margolis DA, Smith KY, Vanveggel S, Spreen W. Long-acting cabotegravir and rilpivirine dosed every 2 months in adults with HIV-1 infection (ATLAS-2M), 48-week results: a randomised, multicentre, open-label, phase 3b, non-inferiority study. Lancet. 2021 Dec 19;396(10267):1994-2005. doi: 10.1016/S0140-6736(20)32666-0. Epub 2020 Dec 9. PMID: 33308425.


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8: Swindells S, Andrade-Villanueva JF, Richmond GJ, Rizzardini G, Baumgarten A, Masiá M, Latiff G, Pokrovsky V, Bredeek F, Smith G, Cahn P, Kim YS, Ford SL, Talarico CL, Patel P, Chounta V, Crauwels H, Parys W, Vanveggel S, Mrus J, Huang J, Harrington CM, Hudson KJ, Margolis DA, Smith KY, Williams PE, Spreen WR. Long-Acting Cabotegravir and Rilpivirine for Maintenance of HIV-1 Suppression. N Engl J Med. 2020 Mar 19;382(12):1112-1123. doi: 10.1056/NEJMoa1904398. Epub 2020 Mar 4. PMID: 32130809.


9: Hodge D, Back DJ, Gibbons S, Khoo SH, Marzolini C. Pharmacokinetics and Drug- Drug Interactions of Long-Acting Intramuscular Cabotegravir and Rilpivirine. Clin Pharmacokinet. 2021 Jul;60(7):835-853. doi: 10.1007/s40262-021-01005-1. Epub 2021 Apr 8. PMID: 33830459; PMCID: PMC8249281.


10: LiverTox: Clinical and Research Information on Drug-Induced Liver Injury [Internet]. Bethesda (MD): National Institute of Diabetes and Digestive and Kidney Diseases; 2012–. Cabotegravir. 2023 Jun 17. PMID: 37384749.


11: Engelman KD, Engelman AN. Long-Acting Cabotegravir for HIV/AIDS Prophylaxis. Biochemistry. 2021 Jun 8;60(22):1731-1740. doi: 10.1021/acs.biochem.1c00157. Epub 2021 May 24. PMID: 34029457; PMCID: PMC8515172.


12: Blair HA. Cabotegravir Extended-Release Injectable Suspension: A Review in HIV-1 Pre-Exposure Prophylaxis. Drugs. 2022 Sep;82(14):1489-1498. doi: 10.1007/s40265-022-01791-3. Epub 2022 Oct 18. PMID: 36255686.


13: Prather C, Jeon C. Cabotegravir: The first long-acting injectable for HIV pre-exposure prophylaxis. Am J Health Syst Pharm. 2022 Oct 21;79(21):1898-1905. doi: 10.1093/ajhp/zxac201. PMID: 35894204.


14: Rizzardini G, Overton ET, Orkin C, Swindells S, Arasteh K, Górgolas Hernández-Mora M, Pokrovsky V, Girard PM, Oka S, Andrade-Villanueva JF, Richmond GJ, Baumgarten A, Masiá M, Latiff G, Griffith S, Harrington CM, Hudson KJ, St Clair M, Talarico CL, Patel P, Cutrell A, Van Eygen V, D'Amico R, Mrus JM, Wu S, Ford SL, Chow K, Roberts J, Wills A, Walters N, Vanveggel S, Van Solingen-Ristea R, Crauwels H, Smith KY, Spreen WR, Margolis DA. Long-Acting Injectable Cabotegravir + Rilpivirine for HIV Maintenance Therapy: Week 48 Pooled Analysis of Phase 3 ATLAS and FLAIR Trials. J Acquir Immune Defic Syndr. 2020 Dec 1;85(4):498-506. doi: 10.1097/QAI.0000000000002466. PMID: 33136751; PMCID: PMC7592884.


15: Spinelli MA, Grinsztejn B, Landovitz RJ. Promises and challenges: cabotegravir for preexposure prophylaxis. Curr Opin HIV AIDS. 2022 Jul 1;17(4):186-191. doi: 10.1097/COH.0000000000000733. Epub 2022 Mar 4. PMID: 35762372; PMCID: PMC9240402.


16: Cabotegravir Sodium. Am J Health Syst Pharm. 2021 May 24;78(11):920-924. doi: 10.1093/ajhp/zxab090. PMID: 33821887.


17: Clement ME, Kofron R, Landovitz RJ. Long-acting injectable cabotegravir for the prevention of HIV infection. Curr Opin HIV AIDS. 2020 Jan;15(1):19-26. doi: 10.1097/COH.0000000000000597. PMID: 31644481; PMCID: PMC7382946.


18: Orkin C, Arasteh K, Górgolas Hernández-Mora M, Pokrovsky V, Overton ET, Girard PM, Oka S, Walmsley S, Bettacchi C, Brinson C, Philibert P, Lombaard J, St Clair M, Crauwels H, Ford SL, Patel P, Chounta V, D'Amico R, Vanveggel S, Dorey D, Cutrell A, Griffith S, Margolis DA, Williams PE, Parys W, Smith KY, Spreen WR. Long-Acting Cabotegravir and Rilpivirine after Oral Induction for HIV-1 Infection. N Engl J Med. 2020 Mar 19;382(12):1124-1135. doi: 10.1056/NEJMoa1909512. Epub 2020 Mar 4. PMID: 32130806.


19: Cabotegravir and Rilpivirine. Am J Health Syst Pharm. 2021 May 24;78(11):925-931. doi: 10.1093/ajhp/zxab088. PMID: 33822851.


20: Bettonte S, Berton M, Stader F, Battegay M, Marzolini C. Management of Drug- Drug Interactions Between Long-Acting Cabotegravir and Rilpivirine and Comedications With Inducing Properties: A Modeling Study. Clin Infect Dis. 2023 Apr 3;76(7):1225-1236. doi: 10.1093/cid/ciac901. PMID: 36377436; PMCID: PMC10069847.