ROC/PRD_000454

Saquinavir

Created:	2000-01-04
Last modified:	2020-08-12

ROC/PRD_000454 is described in the Biologically Interesting Molecule Reference Dictionary (BIRD).

The representative PDB ID is 1HXB.

Help Find related ligands:
Similar Ligands (Stereospecific) Similar Ligands (including Stereoisomers) Similar Ligands (Quick Screen) Similar Ligands (Substructure Stereospecific) Similar Ligands (Substructure including Stereoisomers)

Help

Find related ligands:

Similar Ligands (Stereospecific) Similar Ligands (including Stereoisomers) Similar Ligands (Quick Screen) Similar Ligands (Substructure Stereospecific) Similar Ligands (Substructure including Stereoisomers)

Chemical Details
Formal Charge	0
Atom Count	99
Chiral Atom Count	6
Bond Count	103
Aromatic Bond Count	17

Toggle Hydrogen Toggle Labels

Chemical Component Summary
Name	Saquinavir
Synonyms	Fortovase; SAQUINAVIR; RO 31-8959
Systematic Name (OpenEye OEToolkits)	(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
Formula	C₃₈ H₅₀ N₆ O₅
Molecular Weight	670.841
Type	PEPTIDE-LIKE

Chemical Descriptors
Type	Program	Version	Descriptor
SMILES	ACDLabs	12.01	O=C(N)CC(NC(=O)c1nc2c(cc1)cccc2)C(=O)NC(Cc3ccccc3)C(O)CN5C(C(=O)NC(C)(C)C)CC4C(CCCC4)C5
SMILES	CACTVS	3.370	CC(C)(C)NC(=O)[CH]1C[CH]2CCCC[CH]2CN1C[CH](O)[CH](Cc3ccccc3)NC(=O)[CH](CC(N)=O)NC(=O)c4ccc5ccccc5n4
SMILES	OpenEye OEToolkits	1.7.0	CC(C)(C)NC(=O)C1CC2CCCCC2CN1CC(C(Cc3ccccc3)NC(=O)C(CC(=O)N)NC(=O)c4ccc5ccccc5n4)O
Canonical SMILES	CACTVS	3.370	CC(C)(C)NC(=O)[C@@H]1C[C@@H]2CCCC[C@@H]2CN1C[C@@H](O)[C@H](Cc3ccccc3)NC(=O)[C@H](CC(N)=O)NC(=O)c4ccc5ccccc5n4
Canonical SMILES	OpenEye OEToolkits	1.7.0	CC(C)(C)NC(=O)[C@@H]1C[C@@H]2CCCC[C@@H]2C[N@]1C[C@H]([C@H](Cc3ccccc3)NC(=O)[C@H](CC(=O)N)NC(=O)c4ccc5ccccc5n4)O
InChI	InChI	1.03	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	InChI	1.03	QWAXKHKRTORLEM-UGJKXSETSA-N

Drug Info: DrugBank

DrugBank ID	DB01232
Name	Saquinavir
Groups	approved investigational
Description	Saquinavir is an HIV-1 protease inhibitor used in combination with [ritonavir] and other antiretrovirals for the treatment of human immunodeficiency virus-1 (HIV-1) infection. In 1995 it became the first protease inhibitor approved by the FDA, followed shortly by ritonavir in 1996, and remains in clinical use today due to a relatively benign adverse effect profile as compared to other antiretroviral therapies.[A214382] While its efficacy was initially limited by exceptionally poor oral bioavailability (approximately 4%),[L3450] its current indications require the co-administration of ritonavir - a potent enzyme inhibitor - that increases the bioavailability and subsequent serum concentrations of saquinavir, thus dramatically improving antiviral activity.[A214382,L3450,L14351]
Synonyms	Saquinavir Saquinavir mesylate
Brand Names	Invirase - Cap 200mg Fortovase Invirase Fortovase Roche
Indication	Saquinavir is indicated, in combination with ritonavir and other antiretroviral agents, for the treatment of HIV-1 infection in patients 16 years of age and older.[L3450]
Categories	Agents Causing Muscle Toxicity Anti-HIV Agents Anti-Infective Agents Anti-Retroviral Agents Antiinfectives for Systemic Use Antiviral Agents Antivirals for Systemic Use BCRP/ABCG2 Inhibitors BSEP/ABCB11 Substrates Cytochrome P-450 CYP2C8 Inhibitors Cytochrome P-450 CYP2C8 Inhibitors (moderate) Cytochrome P-450 CYP2C8 Inhibitors (strength unknown) Cytochrome P-450 CYP2D6 Inhibitors Cytochrome P-450 CYP2D6 Inhibitors (strength unknown) Cytochrome P-450 CYP2D6 Inhibitors (weak) Cytochrome P-450 CYP3A Inhibitors Cytochrome P-450 CYP3A Substrates Cytochrome P-450 CYP3A4 Inhibitors Cytochrome P-450 CYP3A4 Inhibitors (strong) Cytochrome P-450 CYP3A4 Substrates Cytochrome P-450 CYP3A5 Inhibitors Cytochrome P-450 CYP3A5 Inhibitors (strength unknown) Cytochrome P-450 CYP3A5 Inhibitors (strong) Cytochrome P-450 CYP3A5 Substrates Cytochrome P-450 CYP3A7 Inhibitors Cytochrome P-450 CYP3A7 Inhibitors (strength unknown) Cytochrome P-450 CYP3A7 Inhibitors (strong) Cytochrome P-450 CYP3A7 Inhibitors (weak) Cytochrome P-450 CYP3A7 Substrates Cytochrome P-450 Enzyme Inhibitors Cytochrome P-450 Substrates Direct Acting Antivirals Enzyme Inhibitors Heterocyclic Compounds, Fused-Ring HIV Protease Inhibitors Hyperglycemia-Associated Agents Isoquinolines Moderate Risk QTc-Prolonging Agents OATP1B1/SLCO1B1 Inhibitors OCT1 inhibitors Organic Anion Transporting Polypeptide 2B1 Inhibitors P-glycoprotein inducers P-glycoprotein inhibitors P-glycoprotein substrates Protease Inhibitors QTc Prolonging Agents Quinolines Viral Protease Inhibitors
ATC-Code	J05AE01
CAS number	127779-20-8

Drug Targets

Name	Target Sequence	Pharmacological Action	Actions
Human immunodeficiency virus type 1 protease	PQVTLWQRPLVTIKIGGQLKEALLDTGADDTVLEEMSLPGRWKPKMIGGI...	unknown	inhibitor
Cytochrome P450 2C8	MEPFVVLVLCLSFMLLFSLWRQSCRRRKLPPGPTPLPIIGNMLQIDVKDI...	unknown	inhibitor
Cytochrome P450 2D6	MGLEALVPLAVIVAIFLLLVDLMHRRQRWAARYPPGPLPLPGLGNLLHVD...	unknown	inhibitor
Cytochrome P450 3A4	MALIPDLAMETWLLLAVSLVLLYLYGTHSHGLFKKLGIPGPTPLPFLGNI...	unknown	substrate,inhibitor
Cytochrome P450 3A5	MDLIPNLAVETWLLLAVSLVLLYLYGTRTHGLFKRLGIPGPTPLPLLGNV...	unknown	substrate,inhibitor
Cytochrome P450 3A7	MDLIPNLAVETWLLLAVSLILLYLYGTRTHGLFKKLGIPGPTPLPFLGNA...	unknown	substrate,inhibitor
Alpha-1-acid glycoprotein 1	MALSWVLTVLSLLPLLEAQIPLCANLVPVPITNATLDQITGKWFYIASAF...	unknown
Serum albumin	MKWVTFISLLFLFSSAYSRGVFRRDAHKSEVAHRFKDLGEENFKALVLIA...	unknown
P-glycoprotein 1	MDLEGDRNGGAKKKNFFKLNNKSEKDKKEKKPTVSVFSMFRYSNWLDKLY...	unknown	substrate,inhibitor,inducer
Solute carrier family 22 member 1	MPTVDDILEQVGESGWFQKQAFLILCLLSAAFAPICVGIVFLGFTPDHHC...	unknown	inhibitor
Solute carrier organic anion transporter family member 1A2	MGETEKRIETHRIRCLSKLKMFLLAITCAFVSKTLSGSYMNSMLTQIERQ...	unknown	inhibitor
ATP-binding cassette sub-family G member 2	MSSSNVEVFIPVSQGNTNGFPATASNDLKAFTEGAVLSFHNICYRVKLKS...	unknown	inhibitor
Solute carrier organic anion transporter family member 1B1	MDQNQHLNKTAEAQPSENKKTRYCNGLKMFLAALSLSFIAKTLGAIIMKS...	unknown	inhibitor
Multidrug resistance-associated protein 1	MALRGFCSADGSDPLWDWNVTWNTSNPDFTKCFQNTVLVWVPCFYLWACF...	unknown	substrate
Canalicular multispecific organic anion transporter 1	MLEKFCNSTFWNSSFLDSPEADLPLCFEQTVLVWIPLGYLWLLAPWQLLH...	unknown	substrate
Solute carrier organic anion transporter family member 2B1	MGPRIGPAGEVPQVPDKETKATMGTENTPGGKASPDPQDVRPSVFHNIKL...	unknown	inhibitor
Bile salt export pump	MSDSVILRSIKKFGEENDGFESDKSYNNDKKSRLQDEKKGDGVRVGFFQL...	unknown	substrate
View More

Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682