ID: ALA35505

Max Phase: Phase

Molecular Formula: C8H10N6

Molecular Weight: 190.21

Molecule Type: Small molecule

Representations

Synonyms (2): Dihydralazine | NSC-526654
Synonyms from Alternative Forms(2):

Canonical SMILES:  N/N=c1\[nH][nH]/c(=N\N)c2ccccc12

Standard InChI:  InChI=1S/C8H10N6/c9-11-7-5-3-1-2-4-6(5)8(12-10)14-13-7/h1-4H,9-10H2,(H,11,13)(H,12,14)

Standard InChI Key:  VQKLRVZQQYVIJW-UHFFFAOYSA-N

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: Yes

Availability: No

Prodrug: No

Properties

Molecular Weight: 190.21

Molecular Weight (Monoisotopic): 190.0967

AlogP: -0.96

#Rotatable Bonds: 0

Polar Surface Area: 108.34

Molecular Species: BASE

HBA: 4

HBD: 4

#RO5 Violations: 0

HBA (Lipinski): 6

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 10.41

CX Basic pKa: 9.26

CX LogP: -0.41

CX LogD: -2.60

Aromatic Rings: 2

Heavy Atoms: 14

QED Weighted: 0.32

Np Likeness Score: -0.29

References

1. Lal B, Dohadwalla AN, Dadkar NK, D'Sa A, de Souza NJ..  (1984)  Trequinsin, a potent new antihypertensive vasodilator in the series of 2-(arylimino)-3-alkyl-9,10-dimethoxy-3,4,6,7-tetrahydro-2H-py rim ido [6,1-a]isoquinolin-4-ones.,  27  (11): [PMID:6492077] [10.1021/jm00377a016]

2. Cignarella G, Barlocco D, Pinna GA, Loriga M, Tofanetti O, Germini M, Sala F..  (1986)  Conformationally restricted congeners of hypotensive and platelet aggregation inhibitors: 6-aryl-5-methyl-4,5-dihydro-3(2H)-pyridazinones derived from 5H-indeno[1,2-c]pyridazine.,  29  (11): [PMID:3783580] [10.1021/jm00161a010]

3. Cignarella G, Barlocco D, Pinna GA, Loriga M, Curzu MM, Tofanetti O, Germini M, Cazzulani P, Cavalletti E..  (1989)  Synthesis and biological evaluation of substituted benzo[h]cinnolinones and 3H-benzo[6,7]cyclohepta[1,2-c]pyridazinones: higher homologues of the antihypertensive and antithrombotic 5H-indeno[1,2-c]pyridazinones.,  32  (10): [PMID:2795599] [10.1021/jm00130a009]

4. Steiner G, Gries J, Lenke D..  (1981)  Synthesis and antihypertensive activity of new 6-heteroaryl-3-hydrazinopyridazine derivatives.,  24  (1): [PMID:7205877] [10.1021/jm00133a013]

5. Thyes M, Lehmann HD, Gries J, König H, Kretzschmar R, Kunze J, Lebkücher R, Lenke D..  (1983)  6-Aryl-4,5-dihydro-3(2H)-pyridazinones. A new class of compounds with platelet aggregation inhibiting and hypotensive activities.,  26  (6): [PMID:6854582] [10.1021/jm00360a004]

6. PubChem BioAssay data set, 

7. Fourches D, Barnes JC, Day NC, Bradley P, Reed JZ, Tropsha A..  (2010)  Cheminformatics analysis of assertions mined from literature that describe drug-induced liver injury in different species.,  23  (1): [PMID:20014752] [10.1021/tx900326k]

8. Kruhlak NL, Choi SS, Contrera JF, Weaver JL, Willard JM, Hastings KL, Sancilio LF..  (2008)  Development of a phospholipidosis database and predictive quantitative structure-activity relationship (QSAR) models.,  18  (2): [PMID:20020916] [10.1080/15376510701857262]

9. Fontana E, Dansette PM, Poli SM..  (2005)  Cytochrome p450 enzymes mechanism based inhibitors: common sub-structures and reactivity.,  6  (1): [PMID:16248836] [10.2174/138920005774330639]

10. Biour M, Ben Salem C, Chazouillères O, Grangé JD, Serfaty L, Poupon R..  (2004)  [Drug-induced liver injury; fourteenth updated edition of the bibliographic database of liver injuries and related drugs].,  28  (8-9): [PMID:15646539] [10.1016/s0399-8320(04)95062-2]

11. PubChem BioAssay data set, 

12. PubChem BioAssay data set, 

13. Dawson S, Stahl S, Paul N, Barber J, Kenna JG..  (2012)  In vitro inhibition of the bile salt export pump correlates with risk of cholestatic drug-induced liver injury in humans.,  40  (1): [PMID:21965623] [10.1124/dmd.111.040758]

14. WHO Anatomical Therapeutic Chemical Classification, 

15. Warner DJ, Chen H, Cantin LD, Kenna JG, Stahl S, Walker CL, Noeske T..  (2012)  Mitigating the inhibition of human bile salt export pump by drugs: opportunities provided by physicochemical property modulation, in silico modeling, and structural modification.,  40  (12): [PMID:22961681] [10.1124/dmd.112.047068]

16. Unpublished dataset, 

17. Ellen Van Damme.  (2021)  Screening of ~5500 FDA-approved drugs and clinical candidates for anti-SARS-CoV-2 activity,  [10.6019/CHEMBL4651402]

18. Wu Q, Sun Z, Chen Z, Liu J, Ding H, Luo C, Wang M, Du D..  (2022)  The discovery of a non-competitive GOT1 inhibitor, hydralazine hydrochloride, via a coupling reaction-based high-throughput screening assay.,  73  [PMID:35820623] [10.1016/j.bmcl.2022.128883]

19. Sherrill LM, Joya EE, Walker A, Roy A, Alhammad YM, Atobatele M, Wazir S, Abbas G, Keane P, Zhuo J, Leung AKL, Johnson DK, Lehtiö L, Fehr AR, Ferraris D..  (2022)  Design, synthesis and evaluation of inhibitors of the SARS-CoV-2 nsp3 macrodomain.,  67  [PMID:35597097] [10.1016/j.bmc.2022.116788]

20. Sutherland JJ, Yonchev D, Fekete A, Urban L..  (2023)  A preclinical secondary pharmacology resource illuminates target-adverse drug reaction associations of marketed drugs.,  14  (1): [PMID:37468498] [10.1038/s41467-023-40064-9]

Source

Source(5):

• Scientific Literature
• PubChem BioAssays
• Clinical Candidates
• WHO Anatomical Therapeutic Chemical Classification
• IMI-CARE SARS-CoV-2 Data