BUTAMBEN PICRATE

Possibly Marketed Outside US

First approved in 1958

Details

Stereochemistry	ACHIRAL
Molecular Formula	2C11H15NO2.C6H3N3O7
Molecular Weight	615.5885
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCCCOC(=O)C1=CC=C(N)C=C1.CCCCOC(=O)C2=CC=C(N)C=C2.OC3=C(C=C(C=C3[N+]([O-])=O)[N+]([O-])=O)[N+]([O-])=O

InChI

InChIKey=ATAGSVCDFKGYPE-UHFFFAOYSA-N

InChI=1S/2C11H15NO2.C6H3N3O7/c2*1-2-3-8-14-11(13)9-4-6-10(12)7-5-9;10-6-4(8(13)14)1-3(7(11)12)2-5(6)9(15)16/h2*4-7H,2-3,8,12H2,1H3;1-2,10H

HIDE SMILES / InChI

Molecular Formula	C6H3N3O7
Molecular Weight	229.1039
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Molecular Formula	C11H15NO2
Molecular Weight	193.2423
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=89f262a4-a41b-41d7-806b-61b9b89542f0
Curator's Comment: description was created based on several sources, including: https://en.wikipedia.org/wiki/Butamben

Butamben is a local anesthetic. It is the ester of 4-aminobenzoic acid and butanol. It is one of three components in the topical anesthetic Cetacaine. The onset of Cetacaine-produced anesthesia is rapid (approximately 30 seconds) and the duration of anesthesia is typically 30-60 minutes, when used as directed. This effect is due to the rapid onset, but short duration of action of Benzocaine coupled with the slow onset, but extended duration of Tetracaine HCI and bridged by the intermediate action of Butamben.

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
nerve conduction 2 Target ID: nerve conduction Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=89f262a4-a41b-41d7-806b-61b9b89542f0	Blocker 537

Conditions

Condition	Modality	Targets	Highest Phase	Product
Topical anesthetic 2 Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=89f262a4-a41b-41d7-806b-61b9b89542f0	Primary		Basic research	CETACAINE ANESTHETIC Approved Use Unknown

PubMed

Title	Date	PubMed
Effect of epidural and subarachnoid injections of a 10% butamben suspension.	1990 May-Jun	2265169
Structure-activity relationships for a large diverse set of natural, synthetic, and environmental estrogens.	2001 Mar	11258977
The antinociceptive and histologic effect of sciatic nerve blocks with 5% butamben suspension in rats.	2002 Mar	11867403
Benzoate X receptors alpha and beta are pharmacologically distinct and do not function as xenobiotic receptors.	2002 Nov 15	12198127
Study of 202 natural, synthetic, and environmental chemicals for binding to the androgen receptor.	2003 Oct	14565775
Hydrolysis of angiotensin II receptor blocker prodrug olmesartan medoxomil by human serum albumin and identification of its catalytic active sites.	2005 Dec	16183779
The block of total and N-type calcium conductance in mouse sensory neurons by the local anesthetic n-butyl-p-aminobenzoate.	2005 Jun	15920194
Inhibition of the A-type K+ channels of dorsal root ganglion neurons by the long-duration anesthetic butamben.	2005 Sep	15923341
The local anesthetic butamben inhibits and accelerates low-voltage activated T-type currents in small sensory neurons.	2006 Jan	16368819
Prediction of estrogen receptor agonists and characterization of associated molecular descriptors by statistical learning methods.	2006 Nov	16497524
The local anesthetic butamben inhibits total and L-type barium currents in PC12 cells.	2008 Jun	18499609
High concentrations of morphine sensitize and activate mouse dorsal root ganglia via TRPV1 and TRPA1 receptors.	2009 Apr 16	19371406
Regional & topical anaesthesia of upper airways.	2009 Dec	20640090
Alveolar osteitis: a comprehensive review of concepts and controversies.	2010	20652078
New "drug-in cyclodextrin-in deformable liposomes" formulations to improve the therapeutic efficacy of local anaesthetics.	2010 Aug 16	20594944
The evolution of farnesoid X, vitamin D, and pregnane X receptors: insights from the green-spotted pufferfish (Tetraodon nigriviridis) and other non-mammalian species.	2011 Feb 3	21291553

Patents

Sample Use Guides

In Vivo Use Guide

Cetacaine Spray: approximately one second or less for normal anesthesia Cetacaine Liquid: 200 mg (approximately 0.2 mL) with a cotton applicator or directly to tissue Cetacaine Gel: 200 mg of gel (a bead approximately 1/4 to 1/2 inches long) by gently depressing the pump

Route of Administration: Topical

In Vitro Use Guide

Butamben 500 uM reversibly suppressed the total whole-cell barium current by 90% +/- 3% through expressed calcium channel types in PC12 cells, including Cav1.2/L-type channels

Substance Class	Chemical Created by `admin` on `Fri Dec 15 17:48:32 GMT 2023` Edited by `admin` on `Fri Dec 15 17:48:32 GMT 2023`
Record UNII	D4ZFB7ZH5Y
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

BUTAMBEN PICRATE

Official Name

English

BUTAMBEN PICRATE [USAN]

Common Name

English

BUTAMBEN PICRATE [VANDF]

Common Name

English

BENZOIC ACID, 4-AMINO-, BUTYL ESTER, COMPOUND WITH 2,4,6-TRINITROPHENOL (2:1)

Systematic Name

English

BUTYL P-AMINOBENZOATE, PICRATE (2:1)

Common Name

English

BUTYL AMINOBENZOATE PICRATE [MART.]

Common Name

English

ABBOTT-34842

Code

English

Butyl aminobenzoate picrate [WHO-DD]

Common Name

English

BUTYL AMINOBENZOATE PICRATE

Systematic Name

English

Classification Tree Code System Code

NCI_THESAURUS

C245