Details of the Drug

General Information of Drug (ID: DM4LSNE)

Drug Name

Procaine

Synonyms

Allocaine; Anticort; Anuject; Duracaine; Gerokit; Gerovital; Jenacain; Jenacaine; Nissocaine; Norocaine; Novocain; Novocaine; Procain; Procaina; Procainum; Scurocaine; Spinocaine; Solution of novocain; Factor H3; SP01; SP01A; Stoff H3; Vitamin H3; Anticort (TM); Diethylaminoethyl p-aminobenzoate; Gerovital H-3; Novocain (TN); P-Aminobenzoyldiethylaminoethanol; P-Aminobenzyoyldiethylaminoethanol; Procaina [INN-Spanish]; Procaine (INN); Procaine [INN:BAN]; Procaine, base; Procainum [INN-Latin]; SP-01A; Solution of novocain (TN); Beta-Diethylaminoethyl 4-aminobenzoate; P-Aminobenzoic acid 2-diethylaminoethyl ester; Beta-(Diethylamino)ethyl 4-aminobenzoate; Beta-(Diethylamino)ethyl p-aminobenzoate; BENZOIC ACID,4-AMINO,2-DIETHYLAMINOETHYL ESTER PROCAIN BASE; Benzoic acid, 4-amino-, 2-(diethylamino)ethyl ester; Benzoic acid, p-amino-, 2-(diethylamino)ethyl ester; 2-(Diethylamino)ethyl 4-aminobenzoate; 2-(Diethylamino)ethyl p-aminobenzoate; 2-(Diethylamino)ethyl-4-aminobenzoate; 2-Diethylaminoethyl 4-aminobenzoate; 2-Diethylaminoethyl p-aminobenzoate; 2-Diethylaminoethylester kyseliny p-aminobenzoove; 2-Diethylaminoethylester kyseliny p-aminobenzoove [Czech]; 4-Aminobenzoesaeure-beta-diethylaminoethylester; 4-Aminobenzoic acid 2-(diethylamino) ethyl ester; 4-Aminobenzoic acid diethylaminoethyl ester

Indication

Disease Entry	ICD 11	Status	REF
Anaesthesia	9A78.6	Approved	[1]

Therapeutic Class

Anesthetics

Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 0

Molecular Weight (mw)

236.31

Topological Polar Surface Area (xlogp)

1.9

Rotatable Bond Count (rotbonds)

7

Hydrogen Bond Donor Count (hbonddonor)

1

Hydrogen Bond Acceptor Count (hbondacc)

4

ADMET Property

Half-life: The concentration or amount of drug in body reduced by one-half in 7.7 minutes [2]
Metabolism: The drug is metabolized via plasma esterases [3]
MRTD: The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 60.4507 micromolar/kg/day [4]

Chemical Identifiers

Formula: C13H20N2O2
IUPAC Name: 2-(diethylamino)ethyl 4-aminobenzoate
Canonical SMILES: CCN(CC)CCOC(=O)C1=CC=C(C=C1)N
InChI: InChI=1S/C13H20N2O2/c1-3-15(4-2)9-10-17-13(16)11-5-7-12(14)8-6-11/h5-8H,3-4,9-10,14H2,1-2H3
InChIKey: MFDFERRIHVXMIY-UHFFFAOYSA-N

Cross-matching ID

PubChem CID: 4914
ChEBI ID: CHEBI:8430
CAS Number: 59-46-1
DrugBank ID: DB00721
TTD ID: D0TZ1G
ACDINA ID: D01361

Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
5-HT 3A receptor (HTR3A)	TTPC4TU	5HT3A_HUMAN	Antagonist	[5]

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Molecular Interaction Atlas (MIA)

MIA Detail

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Molecular Expression Atlas of This Drug

The Studied Disease

Anaesthesia

ICD Disease Classification

9A78.6

Molecule Name	Molecule Type	Gene Name	p-value	Fold-Change	Z-score
5-HT 3A receptor (HTR3A)	DTT	HTR3A	6.60E-01	1.08E-02	0.04

Molecular Expression Atlas (MEA)

MEA Detail

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Drug-Drug Interaction (DDI) Information of This Drug

Coadministration of a Drug Treating the Same Disease as Procaine

DDI Drug Name	DDI Drug ID	Severity	Mechanism	Disease	REF
Atracurium	DM42HXN	Moderate	Additive neuromuscular blocking effects by the combination of Procaine and Atracurium.	Corneal disease [9A76-9A78]	[15]
Mivacurium	DM473VD	Moderate	Additive neuromuscular blocking effects by the combination of Procaine and Mivacurium.	Corneal disease [9A76-9A78]	[15]
Pancuronium	DMB0VY8	Moderate	Additive neuromuscular blocking effects by the combination of Procaine and Pancuronium.	Corneal disease [9A76-9A78]	[15]
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Coadministration of a Drug Treating the Disease Different from Procaine (Comorbidity)

DDI Drug Name	DDI Drug ID	Severity	Mechanism	Comorbidity	REF
Prilocaine	DMI7DZ2	Major	Increased risk of methemoglobinemia by the combination of Procaine and Prilocaine.	Pain [MG30-MG3Z]	[16]
Vecuronium	DMP0UK2	Moderate	Additive neuromuscular blocking effects by the combination of Procaine and Vecuronium.	Tonus and reflex abnormality [MB47]	[15]
Rocuronium	DMY9BMK	Moderate	Additive neuromuscular blocking effects by the combination of Procaine and Rocuronium.	Tonus and reflex abnormality [MB47]	[15]
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Drug Inactive Ingredient(s) (DIG) and Formulation(s) of This Drug

DIG

DIG Name	DIG ID	PubChem CID	Functional Classification
methylparaben	E00149	7456	Antimicrobial preservative
Propylparaben sodium	E00567	23679044	Antimicrobial preservative
Sodium citrate anhydrous	E00102	6224	Alkalizing agent; Buffering agent; Complexing agent; Emulsifying agent
Povidone	E00667	Not Available	Binding agent; Coating agent; Disintegrant; Film/membrane-forming agent; Solubilizing agent; Suspending agent
Soybean lecithin	E00637	Not Available	Other agent
Carboxymethylcellulose	E00692	Not Available	Adsorbent; Suspending agent; Binding agent; Disintegrant; Viscosity-increasing agent
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⏷ Show the Full List of 6 Pharmaceutical Excipients of This Drug

Pharmaceutical Formulation

Formulation Name	Drug Dosage	Dosage Form	Route
Procaine 300000 units/ml injectable	300000 units/ml	Injectable	Injection

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References

1	Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services. 2015
2	Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
3	FDA approval: ado-trastuzumab emtansine for the treatment of patients with HER2-positive metastatic breast cancer. Clin Cancer Res. 2014 Sep 1;20(17):4436-41.
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	Local anesthetics have different mechanisms and sites of action at recombinant 5-HT3 receptors. Reg Anesth Pain Med. 2007 Nov-Dec;32(6):462-70.
6	Palonosetron plus dexamethasone versus granisetron plus dexamethasone for prevention of nausea and vomiting during chemotherapy: a double-blind, do... Lancet Oncol. 2009 Feb;10(2):115-24.
7	Efficacy of 5-HT3 antagonists and 5-HT4 agonists in irritable bowel syndrome: systematic review and meta-analysis. Am J Gastroenterol. 2009 Jul;104(7):1831-43; quiz 1844.
8	Emerging therapies for fibromyalgia. Expert Opin Emerg Drugs. 2008 Mar;13(1):53-62.
9	Management of postoperative nausea and vomiting: focus on palonosetron. Ther Clin Risk Manag. 2009 Feb;5(1):21-34.
10	2018 FDA drug approvals.Nat Rev Drug Discov. 2019 Feb;18(2):85-89.
11	Cilansetron: a new serotonergic agent for the irritable bowel syndrome with diarrhoea.Expert Opin Investig Drugs.2005 Feb;14(2):185-93.
12	Zatosetron, a potent, selective, and long-acting 5HT3 receptor antagonist: synthesis and structure-activity relationships. J Med Chem. 1992 Jan 24;35(2):310-9.
13	mu-Opioid/5-HT4 dual pharmacologically active agents-efforts towards an effective opioid analgesic with less GI and respiratory side effects (Part I). Bioorg Med Chem Lett. 2009 Oct 1;19(19):5679-83.
14	Effect of serotonin (5-HT)3-receptor antagonists YM060, YM114 (KAE-393), ondansetron and granisetron on 5-HT4 receptors and gastric emptying in rodents. Jpn J Pharmacol. 1995 Nov;69(3):205-14.
15	Multum Information Services, Inc. Expert Review Panel.
16	Agencia Espaola de Medicamentos y Productos Sanitarios Healthcare "Centro de informacion online de medicamentos de la AEMPS - CIMA.".