Details of the Drug

General Information of Drug (ID: DM5F84A)

Drug Name

Pipecuronium

Synonyms

Arduan; Pipecurium; Arduan (TN); Piperazinium, 4,4'-((2beta,3alpha,5alpha,16beta,17beta)-3,17-bis(acetyloxy)androstane-2,16-diyl)bis(1,1-dimethyl); [(2S,3S,5S,8R,9S,10S,13S,14S,16S,17R)-17-acetyloxy-2,16-bis(4,4-dimethylpiperazin-4-ium-1-yl)-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl] acetate

Indication

Disease Entry	ICD 11	Status	REF
Spasm	MB47.3	Approved	[1]
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Therapeutic Class

Analgesics

Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 1

Molecular Weight (mw)

602.9

Logarithm of the Partition Coefficient (xlogp)

4.5

Rotatable Bond Count (rotbonds)

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

ADMET Property

BDDCS Class: Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 3: high solubility and low permeability [2]
Clearance: The drug present in the plasma can be removed from the body at the rate of 3 mL/min/kg [3]
Elimination: 39% of drug is excreted from urine in the unchanged form [2]
Half-life: The concentration or amount of drug in body reduced by one-half in 1.34 - 10.66 (in normal renal function subjects) [3]
MRTD: The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 0.118 micromolar/kg/day [4]
Unbound Fraction: The unbound fraction of drug in plasma is 0.98% [3]
Vd: Fluid volume that would be required to contain the amount of drug present in the body at the same concentration as in the plasma 0.35 L/kg [3]

Chemical Identifiers

Formula: C35H62N4O4+2
IUPAC Name: [(2S,3S,5S,8R,9S,10S,13S,14S,16S,17R)-17-acetyloxy-2,16-bis(4,4-dimethylpiperazin-4-ium-1-yl)-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl] acetate
Canonical SMILES: CC(=O)O[C@H]1C[C@@H]2CC[C@@H]3[C@@H]([C@]2(C[C@@H]1N4CC[N+](CC4)(C)C)C)CC[C@]5([C@H]3C[C@@H]([C@@H]5OC(=O)C)N6CC[N+](CC6)(C)C)C
InChI: InChI=1S/C35H62N4O4/c1-24(40)42-32-21-26-9-10-27-28(35(26,4)23-31(32)37-15-19-39(7,8)20-16-37)11-12-34(3)29(27)22-30(33(34)43-25(2)41)36-13-17-38(5,6)18-14-36/h26-33H,9-23H2,1-8H3/q+2/t26-,27+,28-,29-,30-,31-,32-,33-,34-,35-/m0/s1
InChIKey: OWWLUIWOFHMHOQ-XGHATYIMSA-N

Cross-matching ID

PubChem CID: 50192
ChEBI ID: CHEBI:8230
CAS Number: 68399-58-6
DrugBank ID: DB01338
TTD ID: D0XX6Y

Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
Neuronal acetylcholine receptor alpha-2 (CHRNA2)	TTF4E0J	ACHA2_HUMAN	Antagonist	[5]

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Molecular Interaction Atlas (MIA)

MIA Detail

Jump to Detail Molecular Interaction Atlas of This Drug

Drug-Drug Interaction (DDI) Information of This Drug

Coadministration of a Drug Treating the Same Disease as Pipecuronium

DDI Drug Name	DDI Drug ID	Severity	Mechanism	Disease	REF
Vecuronium	DMP0UK2	Moderate	Additive neuromuscular blocking effects by the combination of Pipecuronium and Vecuronium.	Tonus and reflex abnormality [MB47]	[6]
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Coadministration of a Drug Treating the Disease Different from Pipecuronium (Comorbidity)

DDI Drug Name	DDI Drug ID	Severity	Mechanism	Comorbidity	REF
Paromomycin	DM1AGXN	Major	Additive neuromuscular blocking effects by the combination of Pipecuronium and Paromomycin.	Amoebiasis [1A36]	[7]
Lincomycin	DMVTHER	Moderate	Additive neuromuscular blocking effects by the combination of Pipecuronium and Lincomycin.	Gram-positive bacterial infection [1B74-1F40]	[8]
Nebivolol	DM7F1PA	Moderate	Additive neuromuscular blocking effects by the combination of Pipecuronium and Nebivolol.	Hypertension [BA00-BA04]	[9]
Plazomicin	DMKMBES	Major	Additive neuromuscular blocking effects by the combination of Pipecuronium and Plazomicin.	Urinary tract infection [GC08]	[10]
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References

1	Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services. 2015
2	BDDCS applied to over 900 drugs
3	Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
4	Estimating the safe starting dose in phase I clinical trials and no observed effect level based on QSAR modeling of the human maximum recommended daily dose
5	Synergy between pairs of competitive antagonists at adult human muscle acetylcholine receptors. Anesth Analg. 2008 Aug;107(2):525-33.
6	Pandit SK, Ferres CJ, Gibson FM, Mirakhur RK "Time course of action of combinations of vecuronium and pancuronium." Anaesthesia 41 (1986): 151-4. [PMID: 2869710]
7	Burkett L, Bikhazi GB, Thomas KC Jr, Rosenthal DA, Wirta MG, Foldes FF "Mutual potentiation of the neuromuscular effects of antibiotics and relaxants." Anesth Analg 58 (1979): 107-15. [PMID: 571233]
8	Alahdal O, Bevan DR "Clindamycin-induced neuromuscular blockade." Can J Anaesth 42 (1995): 614-7. [PMID: 7553999]
9	Chapple DJ, Clark JS, Hughes R "Interaction between atracurium and drugs used in anaesthesia." Br J Anaesth 55 Suppl 1 (1983): s17-22. [PMID: 6688011]
10	Geha DG, Blitt CD, Moon BJ "Prolonged neuromuscular blockade with pancuronium in the presence of acute renal failure: a case report." Anesth Analg 55 (1976): 343-5. [PMID: 945014]