ID: ALA3707183

Max Phase: Approved

First Approval: 1962

Molecular Formula: C40H54N4O10S

Molecular Weight: 324.42

Molecule Type: Small molecule

Representations

Synonyms (12): Quinidex extentabs | Quinidine sulfate | Quinidine sulfate dihydrate | Quinidine sulfate hydrate | Quinidine sulphate | Quinidine sulphate anhydrous | Quinidine sulphate dihydrate | Quinidine, sulfate (2:1) (salt) | Quinidini sulfas | AVP-786 COMPONENT QUINIDINE SULFATE | NSC-10004 | QUINIDINE SULFATE COMPONENT OF AVP-786
Synonyms from Alternative Forms(12):

Trade Names(5): Cin-quin | Quinicardine | Quinidex | Quinidine sulfate | Quinora

Canonical SMILES:  C=C[C@H]1CN2CC[C@H]1C[C@@H]2[C@@H](O)c1ccnc2ccc(OC)cc12.C=C[C@H]1CN2CC[C@H]1C[C@@H]2[C@@H](O)c1ccnc2ccc(OC)cc12.O.O.O=S(=O)(O)O

Standard InChI:  InChI=1S/2C20H24N2O2.H2O4S.2H2O/c2*1-3-13-12-22-9-7-14(13)10-19(22)20(23)16-6-8-21-18-5-4-15(24-2)11-17(16)18;1-5(2,3)4;;/h2*3-6,8,11,13-14,19-20,23H,1,7,9-10,12H2,2H3;(H2,1,2,3,4);2*1H2/t2*13-,14-,19+,20-;;;/m00.../s1

Standard InChI Key:  ZHNFLHYOFXQIOW-AHSOWCEXSA-N

Molecule Features

Natural Product: No

Oral: Yes

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: Yes

Chirality: Yes

Availability: Yes

Prodrug: No

Properties

Molecular Weight: 324.42

Molecular Weight (Monoisotopic): 324.1838

AlogP: 3.17

#Rotatable Bonds: 4

Polar Surface Area: 45.59

Molecular Species: BASE

HBA: 4

HBD: 1

#RO5 Violations: 0

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 13.89

CX Basic pKa: 9.05

CX LogP: 2.51

CX LogD: 0.86

Aromatic Rings: 2

Heavy Atoms: 24

QED Weighted: 0.88

Np Likeness Score: 0.83

References

1. Tripathi RC, Pandey SK, Kar K, Dikshit M, Saxena AK..  (1999)  Synthesis and SAR studies of 1-substituted-n-(4-alkoxycarbonylpiperidin-1-yl)alkanes as potent antiarrhythmic agents.,  9  (18): [PMID:10509918] [10.1016/s0960-894x(99)00456-4]

2. Voets M, Antes I, Scherer C, Müller-Vieira U, Biemel K, Barassin C, Marchais-Oberwinkler S, Hartmann RW..  (2005)  Heteroaryl-substituted naphthalenes and structurally modified derivatives: selective inhibitors of CYP11B2 for the treatment of congestive heart failure and myocardial fibrosis.,  48  (21): [PMID:16220979] [10.1021/jm0503704]

3. de Graaf C, Oostenbrink C, Keizers PH, van der Wijst T, Jongejan A, Vermeulen NP..  (2006)  Catalytic site prediction and virtual screening of cytochrome P450 2D6 substrates by consideration of water and rescoring in automated docking.,  49  (8): [PMID:16610785] [10.1021/jm0508538]

4. Tan GT, Pezzuto JM, Kinghorn AD, Hughes SH..  (1991)  Evaluation of natural products as inhibitors of human immunodeficiency virus type 1 (HIV-1) reverse transcriptase.,  54  (1): [PMID:1710653] [10.1021/np50073a012]

5. Yuan J, Johnson RL, Huang R, Wichterman J, Jiang H, Hayton K, Fidock DA, Wellems TE, Inglese J, Austin CP, Su XZ..  (2009)  Genetic mapping of targets mediating differential chemical phenotypes in Plasmodium falciparum.,  5  (10): [PMID:19734910] [10.1038/nchembio.215]

6. Diamandis P, Wildenhain J, Clarke ID, Sacher AG, Graham J, Bellows DS, Ling EK, Ward RJ, Jamieson LG, Tyers M, Dirks PB..  (2007)  Chemical genetics reveals a complex functional ground state of neural stem cells.,  3  (5): [PMID:17417631] [10.1038/nchembio873]

7. Lucumi E, Darling C, Jo H, Napper AD, Chandramohanadas R, Fisher N, Shone AE, Jing H, Ward SA, Biagini GA, DeGrado WF, Diamond SL, Greenbaum DC..  (2010)  Discovery of potent small-molecule inhibitors of multidrug-resistant Plasmodium falciparum using a novel miniaturized high-throughput luciferase-based assay.,  54  (9): [PMID:20547797] [10.1128/aac.00431-10]

8. Unpublished dataset, 

9. USP Dictionary of USAN and International Names (2010 edition) and USAN registrations 2007-date, 

10. Russo CM, Adhikari AA, Wallach DR, Fernandes S, Balch AN, Kerr WG, Chisholm JD..  (2015)  Synthesis and initial evaluation of quinoline-based inhibitors of the SH2-containing inositol 5'-phosphatase (SHIP).,  25  (22): [PMID:26453006] [10.1016/j.bmcl.2015.09.034]

11. British National Formulary (72nd edition), 

12. Unpublished dataset, 

Source

Source(5):

• Scientific Literature
• Clinical Candidates
• FDA Approved Drug Products with Therapeutic Equivalence Evaluations (Orange Book)
• USP Dictionary of USAN and International Drug Names
• British National Formulary