Drug Information

General Information
Drug ID
DR00309
Drug Name
Saquinavir
Synonyms
(2S)-N-[(2S,3R)-4-[(3S,4aS,8aS)-3-(tert-butylcarbamoyl)-3,4,4a,5,6,7,8,8a-octahydro-1H-isoquinolin-2-yl]-3-hydroxy-1-phenylbutan-2-yl]-2-(quinoline-2-carbonylamino)butanediamide; (2s)-N-[(2s,3r)-4-[(2s,3s,4as,8as)-3-(Tert-Butylcarbamoyl)-3,4,4a,5,6,7,8,8a-Octahydro-1h-Isoquinolin-2-Yl]-3-Hydroxy-1-Phenyl-Butan-2-Yl]-2-(Quinolin-2-Ylcarbonylamino)butanediamide; CIS-N-TERT-BUTYL-DECAHYDRO-2-[2(R)-HYDROXY-4-PHENYL-3(S)-[[N-2-QUINOLYLCARBONYL-L-ASPARAGINYL]AMINO]BUTYL]-(4AS)-ISOQUINOLINE-3(S)-CARBOXAMIDE; Fortovase; Fortovase (TN); Fortovase(TM); Invirase; Invirase (TN); Invirase(TM)(monomesylate); QNC-ASN-HPH-DIQ-NTB; ROC; Ro 31-8959; Ro 318959; Ro-31-8959; SQV; Saguinavir; Saquinavir (JAN/USP/INN)
Drug Type
Small molecular drug
Indication Human immunodeficiency virus infection [ICD11:1C62.Z] Approved [1]
Therapeutic Class
Anti-HIV Agents
Structure
3D MOL 2D MOL
Formula
C38H50N6O5
Canonical SMILES
CC(C)(C)NC(=O)C1CC2CCCCC2CN1CC(C(CC3=CC=CC=C3)NC(=O)C(CC(=O)N)NC(=O)C4=NC5=CC=CC=C5C=C4)O
InChI
InChI=1S/C38H50N6O5/c1-38(2,3)43-37(49)32-20-26-14-7-8-15-27(26)22-44(32)23-33(45)30(19-24-11-5-4-6-12-24)41-36(48)31(21-34(39)46)42-35(47)29-18-17-25-13-9-10-16-28(25)40-29/h4-6,9-13,16-18,26-27,30-33,45H,7-8,14-15,19-23H2,1-3H3,(H2,39,46)(H,41,48)(H,42,47)(H,43,49)/t26-,27+,30-,31-,32-,33+/m0/s1
InChIKey
QWAXKHKRTORLEM-UGJKXSETSA-N
CAS Number
CAS 127779-20-8
Pharmaceutical Properties Molecular Weight 670.8 Topological Polar Surface Area 167
Heavy Atom Count 49 Rotatable Bond Count 13
Hydrogen Bond Donor Count 5 Hydrogen Bond Acceptor Count 7
XLogP
4.2
PubChem CID
441243
PubChem SID
10298771 ,103179606 ,104624996 ,104829254 ,11467142 ,11468262 ,11486850 ,117695825 ,14790389 ,14912870 ,24424137 ,24424140 ,24424146 ,24424150 ,26706895 ,36885127 ,46392170 ,46394116 ,46394117 ,47720800 ,47869868 ,48169598 ,48243608 ,49666064 ,49699303 ,49743129 ,49743137 ,49746604 ,50070617 ,50105601 ,53790242 ,56320473 ,57403600 ,596481 ,74519778 ,7847495 ,7890157 ,7890295 ,7980558 ,8030420 ,830611 ,838962 ,85177047 ,85788913 ,92715215 ,93166481 ,93167028 ,93617413 ,93617549 ,99453891
ChEBI ID
CHEBI:63621
TTD Drug ID
D0WI3T
DT(s) Transporting This Drug BCRP Transporter Info Breast cancer resistance protein Substrate [2]
MRP1 Transporter Info Multidrug resistance-associated protein 1 Substrate [3]
MRP2 Transporter Info Multidrug resistance-associated protein 2 Substrate [4]
OATP1A2 Transporter Info Organic anion transporting polypeptide 1A2 Substrate [5]
OATP1B1 Transporter Info Organic anion transporting polypeptide 1B1 Substrate [6]
P-GP Transporter Info P-glycoprotein 1 Substrate [7]
Drug-Transporter Activity Data
Drug-Transporter Activity Data OATP1A2 Transporter Info Km =36.4 microM Oocytes-OATP1A2 [5]
P-GP Transporter Info Km =15.4 microM Human enterocyte-like 2 cells (Caco-2)-MDR1 [7]
P-GP Transporter Info Km =14.5 microM LLC-PK1 cells-MDR1 [8]
References
1 Saquinavir was approved by FDA. The official website of the U.S. Food and Drug Administration. (2019)
2 Nicotine and cotinine increases the brain penetration of saquinavir in rat. J Neurochem. 2010 Dec;115(6):1495-507.
3 Direct evidence that saquinavir is transported by multidrug resistance-associated protein (MRP1) and canalicular multispecific organic anion transporter (MRP2). Antimicrob Agents Chemother. 2002 Nov;46(11):3456-62.
4 Evidence for two interacting ligand binding sites in human multidrug resistance protein 2 (ATP binding cassette C2). J Biol Chem. 2003 Jun 27;278(26):23538-44.
5 Human organic anion-transporting polypeptide OATP-A (SLC21A3) acts in concert with P-glycoprotein and multidrug resistance protein 2 in the vectorial transport of Saquinavir in Hep G2 cells. Mol Pharm. 2004 Jan 12;1(1):49-56.
6 Organic anion transporting polypeptide 1B1: a genetically polymorphic transporter of major importance for hepatic drug uptake. Pharmacol Rev. 2011 Mar;63(1):157-81.
7 Predicting P-glycoprotein effects on oral absorption: correlation of transport in Caco-2 with drug pharmacokinetics in wild-type and mdr1a(-/-) mice in vivo. Pharm Res. 2004 May;21(5):819-26.
8 MDR1 G1199A polymorphism alters permeability of HIV protease inhibitors across P-glycoprotein-expressing epithelial cells. AIDS. 2005 Oct 14;19(15):1617-25.

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