BUTAMBEN PICRATE

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

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 555

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
The evolution of farnesoid X, vitamin D, and pregnane X receptors: insights from the green-spotted pufferfish (Tetraodon nigriviridis) and other non-mammalian species.	2011-02-03	21291553
New "drug-in cyclodextrin-in deformable liposomes" formulations to improve the therapeutic efficacy of local anaesthetics.	2010-08-16	20594944
Alveolar osteitis: a comprehensive review of concepts and controversies.	2010	20652078
Regional & topical anaesthesia of upper airways.	2009-12	20640090
High concentrations of morphine sensitize and activate mouse dorsal root ganglia via TRPV1 and TRPA1 receptors.	2009-04-16	19371406
The local anesthetic butamben inhibits total and L-type barium currents in PC12 cells.	2008-06	18499609
Prediction of estrogen receptor agonists and characterization of associated molecular descriptors by statistical learning methods.	2006-11	16497524
The local anesthetic butamben inhibits and accelerates low-voltage activated T-type currents in small sensory neurons.	2006-01	16368819
Hydrolysis of angiotensin II receptor blocker prodrug olmesartan medoxomil by human serum albumin and identification of its catalytic active sites.	2005-12	16183779
Inhibition of the A-type K+ channels of dorsal root ganglion neurons by the long-duration anesthetic butamben.	2005-09	15923341
Structural characteristics and crystal polymorphism of three local anaesthetic bases crystal polymorphism of local anaesthetic drugs: part VII.	2005-07-14	15955643
The block of total and N-type calcium conductance in mouse sensory neurons by the local anesthetic n-butyl-p-aminobenzoate.	2005-06	15920194
Study of 202 natural, synthetic, and environmental chemicals for binding to the androgen receptor.	2003-10	14565775
Analgesic synergy between topical morphine and butamben in mice.	2003-10	14500165
Analysis of a glucose tetrasaccharide elevated in Pompe disease by stable isotope dilution-electrospray ionization tandem mass spectrometry.	2003-05-15	12711338
Kv1.1 channels of dorsal root ganglion neurons are inhibited by n-butyl-p-aminobenzoate, a promising anesthetic for the treatment of chronic pain.	2003-02	12538804
Benzoate X receptors alpha and beta are pharmacologically distinct and do not function as xenobiotic receptors.	2002-11-15	12198127
The antinociceptive and histologic effect of sciatic nerve blocks with 5% butamben suspension in rats.	2002-03	11867403
Structure-activity relationships for a large diverse set of natural, synthetic, and environmental estrogens.	2001-03	11258977
Effect of epidural and subarachnoid injections of a 10% butamben suspension.	1990-05-01	2265169

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

Name

Type

Language

BUTAMBEN PICRATE

Official Name

English

BUTYL AMINOBENZOATE PICRATE

Preferred 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

Classification Tree Code System Code

NCI_THESAURUS

C245