Details of the Drug

General Information of Drug (ID: DM9UCJK)

Drug Name

Doripenem

Synonyms

Doribax; S 4661; S-4661; Doripenem (USAN/INN); (4R,5S,6S)-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-3-[(3S,5S)-5-[(sulfamoylamino)methyl]pyrrolidin-3-yl]sulfanyl-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid

Indication

Disease Entry	ICD 11	Status	REF
Cholecystitis	N.A.	Approved	[1]
Pyelonephritis	N.A.	Approved	[1]
Urinary tract infection	GC08	Approved	[2]
Gram-positive bacterial infection	1B74-1G40	Phase 3	[3]
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Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 1

Molecular Weight (mw)

420.5

Logarithm of the Partition Coefficient (xlogp)

-3.4

Rotatable Bond Count (rotbonds)

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

ADMET Property

Clearance: The clearance of drug is 10.3 L/h []
Half-life: The concentration or amount of drug in body reduced by one-half in 1 hour [4]
Metabolism: The drug is metabolized via the dehydropeptidase-I into a microbiologically inactive ring-opened metabolite doripenem-M1 []
Unbound Fraction: The unbound fraction of drug in plasma is 0.92% [4]
Vd: The volume of distribution (Vd) of drug is 16.8 L []

Chemical Identifiers

Formula: C15H24N4O6S2
IUPAC Name: (4R,5S,6S)-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-3-[(3S,5S)-5-[(sulfamoylamino)methyl]pyrrolidin-3-yl]sulfanyl-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid
Canonical SMILES: C[C@@H]1[C@@H]2[C@H](C(=O)N2C(=C1S[C@H]3C[C@H](NC3)CNS(=O)(=O)N)C(=O)O)[C@@H](C)O
InChI: InChI=1S/C15H24N4O6S2/c1-6-11-10(7(2)20)14(21)19(11)12(15(22)23)13(6)26-9-3-8(17-5-9)4-18-27(16,24)25/h6-11,17-18,20H,3-5H2,1-2H3,(H,22,23)(H2,16,24,25)/t6-,7-,8+,9+,10-,11-/m1/s1
InChIKey: AVAACINZEOAHHE-VFZPANTDSA-N

Cross-matching ID

PubChem CID: 73303
ChEBI ID: CHEBI:135928
CAS Number: 148016-81-3
DrugBank ID: DB06211
TTD ID: D03QWT
INTEDE ID: DR0534

Repurposed Drugs (RPD)

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Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
Bacterial Dihydropteroate synthetase (Bact folP)	TT4ILYC	DHPS_ECOLI	Inhibitor	[3]

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Drug-Metabolizing Enzyme (DME)

DME Name	DME ID	UniProt ID	MOA	REF
Dehydropeptidase-I (DPEP1)	DEAMVR3	DPEP1_HUMAN	Substrate	[5]
Beta-lactamase (blaB)	DEC3G7M	A0A1S7IV31_ENTAS	Substrate	[6]

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Molecular Interaction Atlas (MIA)

MIA Detail

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References

1	Doripenem FDA Label
2	2007 FDA drug approvals: a year of flux. Nat Rev Drug Discov. 2008 Feb;7(2):107-9.
3	Emerging drugs for bacterial urinary tract infections. Expert Opin Emerg Drugs. 2005 May;10(2):275-98.
4	Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
5	Disposition, metabolism, and excretion of [14C]doripenem after a single 500-milligram intravenous infusion in healthy men. Antimicrob Agents Chemother. 2008 Oct;52(10):3478-83.
6	FRI-4 carbapenemase-producing Enterobacter cloacae complex isolated in Tokyo, Japan. J Antimicrob Chemother. 2018 Nov 1;73(11):2969-2972.