Details of the Drug

General Information of Drug (ID: DMPNTDL)

Drug Name
Seratrodast
Synonyms
Bronica; A 73001; AA 2414; ABT 001; Abbott 73001; A-73001; AA-2414; ABT-001; Abbott-73001; Bronica (TN); Seratrodast [USAN:INN]; Seratrodast (JAN/USAN/INN); (+-)-2,4,5-Trimethyl-3,6-dioxo-zeta-phenyl-1,4-cyclohexadiene-1-heptanoic acid; (+-)-7-(3,5,6-Trimethyl-1,4-benzoquinon-2-yl)-7-phenylheptanoic acid; 7-(3,5,6-trimethyl-1,4-benzoquinon-2-yl)-7-phenylheptanoic acid; 7-phenyl-7-(2,4,5-trimethyl-3,6-dioxocyclohexa-1,4-dien-1-yl)heptanoic acid
Indication
Disease Entry ICD 11 Status REF
Allergic asthma CA23.0 Discontinued in Phase 3 [1]
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 354.4
Logarithm of the Partition Coefficient (xlogp) 4.4
Rotatable Bond Count (rotbonds) 8
Hydrogen Bond Donor Count (hbonddonor) 1
Hydrogen Bond Acceptor Count (hbondacc) 4
Chemical Identifiers
Formula
C22H26O4
IUPAC Name
7-phenyl-7-(2,4,5-trimethyl-3,6-dioxocyclohexa-1,4-dien-1-yl)heptanoic acid
Canonical SMILES
CC1=C(C(=O)C(=C(C1=O)C)C(CCCCCC(=O)O)C2=CC=CC=C2)C
InChI
InChI=1S/C22H26O4/c1-14-15(2)22(26)20(16(3)21(14)25)18(17-10-6-4-7-11-17)12-8-5-9-13-19(23)24/h4,6-7,10-11,18H,5,8-9,12-13H2,1-3H3,(H,23,24)
InChIKey
ZBVKEHDGYSLCCC-UHFFFAOYSA-N
Cross-matching ID
PubChem CID
2449
ChEBI ID
CHEBI:32126
CAS Number
112665-43-7
DrugBank ID
DB06739
TTD ID
D04SPK
INTEDE ID
DR1474
Combinatorial Drugs (CBD) Click to Jump to the Detailed CBD Information of This Drug

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Thromboxane A2 receptor (TBXA2R) TT2O84V TA2R_HUMAN Antagonist [2]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Cytochrome P450 3A4 (CYP3A4) DE4LYSA CP3A4_HUMAN Substrate [3]
Cytochrome P450 2C9 (CYP2C9) DE5IED8 CP2C9_HUMAN Substrate [4]
Mephenytoin 4-hydroxylase (CYP2C19) DEGTFWK CP2CJ_HUMAN Substrate [3]
Cytochrome P450 2B6 (CYP2B6) DEPKLMQ CP2B6_HUMAN Substrate [5]
Cytochrome P450 2C8 (CYP2C8) DES5XRU CP2C8_HUMAN Substrate [3]
Prostaglandin G/H synthase 1 (COX-1) DE073H6 PGH1_HUMAN Substrate [5]
UDP-glucuronosyltransferase 1A9 (UGT1A9) DE85D2P UD19_HUMAN Substrate [5]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

The Studied Disease Allergic asthma
ICD Disease Classification CA23.0
Molecule Name Molecule Type Gene Name p-value Fold-Change Z-score
Thromboxane A2 receptor (TBXA2R) DTT TBXA2R 2.78E-04 -0.11 -0.31
Cytochrome P450 2C8 (CYP2C8) DME CYP2C8 2.93E-03 -2.19E-01 -4.49E-01
Cytochrome P450 2B6 (CYP2B6) DME CYP2B6 4.74E-01 2.25E-01 1.65E-01
Mephenytoin 4-hydroxylase (CYP2C19) DME CYP2C19 1.65E-02 -4.37E-02 -7.84E-02
Cytochrome P450 2C9 (CYP2C9) DME CYP2C9 2.25E-03 -4.98E-01 -6.49E-01
Cytochrome P450 3A4 (CYP3A4) DME CYP3A4 6.90E-01 2.35E-02 7.88E-02
Prostaglandin G/H synthase 1 (COX-1) DME PTGS1 5.11E-09 5.07E-01 9.56E-01
Molecular Expression Atlas (MEA) Jump to Detail Molecular Expression Atlas of This Drug

References

1 Natural products as sources of new drugs over the last 25 years. J Nat Prod. 2007 Mar;70(3):461-77.
2 Thromboxane A2 inhibition: therapeutic potential in bronchial asthma. Am J Respir Med. 2002;1(1):11-7.
3 Identification of cytochromes P450 involved in the human liver microsomal metabolism of the thromboxane A2 inhibitor seratrodast (ABT-001). Drug Metab Dispos. 1997 Jan;25(1):110-5.
4 Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab Rev. 2002 Feb-May;34(1-2):83-448.
5 Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675.