Trimebutine Maleate

Names

[ Name ]:
Trimebutine Maleate

[Synonym ]:
UNII:2A051GM4YM
3,4,5-Trimethoxybenzoic acid 2-(dimethylamino)-2-phenylbutyl ester,Trimebutine maleate salt
(4a,5a,17b)-4,5-Epoxy-3,17-dihydroxyandrost-2-ene-2-carbonitrile
2-(Dimethylamino)-2-phenylbutyl 3,4,5-trimethoxybenzoate maleate
Polybutin
2a-Cyano-4a,5a-epoxyandrostan-17b-ol-3-one
2-(Dimethylamino)-2-phenylbutyl 3,4,5-trimethoxybenzoate (2Z)-2-butenedioate (1:1)
Desopan
Trilostane
Modrenal
EINECS 251-845-9
(1-Ethyl-1-phenyl-2-(3,4,5-trimethoxybenzoyloxy)ethyl)dimethylammonium hydrogen maleate
Benzoic acid, 3,4,5-trimethoxy-, 2-(dimethylamino)-2-phenylbutyl ester, (2Z)-2-butenedioate (1:1)
3,4,5-trimethoxybenzoic acid 2-(dimethylamino)-2-phenylbutyl ester maleate
TM 906 {Maleate}
Benzoic acid, 3,4,5-trimethoxy-, β-(dimethylamino)-β-ethylphenethyl ester, maleate (1:1)
MFCD00133874
Trimebutine Maleate
MODRASTANE
Debridat
2-(Dimethylamino)-2-phenylbutyl 3,4,5-trimethoxybenzoate (2Z)-but-2-enedioate (1:1)
Trimebutine Maleate Salt
(4α,5α,17β)-3,17-Dihydroxy-4,5-epoxyandrost-2-ene-2-carbonitrile
Androst-2-ene-2-carbonitrile, 4,5-epoxy-3,17-dihydroxy-, (4α,5α,17β)-
3,4,5-Trimethoxybenzoic acid 2-(dimethylamino)-2-phenylbutyl ester
Modrefen
3,4,5-Trimethoxybenzoic acid 2-(dimethylamino)-2-phenylbutyl ester maleate salt
Vetoryl
4α,5-Epoxy-3,17β-dihydroxy-5α-androst-2-ene-2-carbonitrile
Recutin
Modulon
Trimebutine (maleate)

Biological Activity

[Description]:

Trimebutine maleate is a drug with antimuscarinic and weak mu opioid agonist effects.Target: Opioid ReceptorTrimebutine is an agonist of peripheral mu, kappa and delta opiate receptors, used as spasmolytic agent for treatment of both acute and chronic abdominal pain [1]. The major product from drug metabolism of trimebutine in human beings is nor-trimebutine, which comes from removal of one of the methyl groups attached to nitrogen. Trimebutine exerts its effects in part due to causing a premature activation of phase III of the migrating motor complex in the digestive tract [2, 3].

[Related Catalog]:

Signaling Pathways >> GPCR/G Protein >> Opioid Receptor

Signaling Pathways >> Neuronal Signaling >> Opioid Receptor

Research Areas >> Metabolic Disease

[References]

[1]. Kaneto, H., M. Takahashi, and J. Watanabe, The opioid receptor selectivity for trimebutine in isolated tissues experiments and receptor binding studies. J Pharmacobiodyn, 1990. 13(7): p. 448-53.

[2]. Roman, F.J., et al., Pharmacological properties of trimebutine and N-monodesmethyltrimebutine. J Pharmacol Exp Ther, 1999. 289(3): p. 1391-7.

[3]. Hiyama, T., et al., Effectiveness of prokinetic agents against diseases external to the gastrointestinal tract. J Gastroenterol Hepatol, 2009. 24(4): p. 537-46.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.3±0.1 g/cm3

[ Boiling Point ]:
497.8±45.0 °C at 760 mmHg

[ Melting Point ]:
122-124ºC

[ Molecular Formula ]:
C₂₆H₃₃NO₉

[ Molecular Weight ]:
503.54

[ Flash Point ]:
254.8±28.7 °C

[ PSA ]:
131.83000

[ LogP ]:
3.61

[ Vapour Pressure ]:
0.0±2.9 mmHg at 25°C

[ Index of Refraction ]:
1.610

[ Storage condition ]:
2-8°C

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: DI0360000

CAS REGISTRY NUMBER :: 34140-59-5

LAST UPDATED :: 199507

DATA ITEMS CITED :: 12

MOLECULAR FORMULA :: C22-H29-N-O5.C4-H4-O4

MOLECULAR WEIGHT :: 503.60

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: >5 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: NIIRDN Drugs in Japan (Ethical Drugs). (Yakugyo Jiho Co., Ltd., Tokyo, Japan) Volume(issue)/page/year: -,752,1990

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 365 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: IYKEDH Iyakuhin Kenkyu. Study of Medical Supplies. (Nippon Koteisho Kyokai, 12-15, 2-chome, Shibuya, Shibuya-ku, Tokyo 150, Japan) V.1- 1970- Volume(issue)/page/year: 15,688,1984

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 3610 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: IYKEDH Iyakuhin Kenkyu. Study of Medical Supplies. (Nippon Koteisho Kyokai, 12-15, 2-chome, Shibuya, Shibuya-ku, Tokyo 150, Japan) V.1- 1970- Volume(issue)/page/year: 15,688,1984

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 23400 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: NIIRDN Drugs in Japan (Ethical Drugs). (Yakugyo Jiho Co., Ltd., Tokyo, Japan) Volume(issue)/page/year: -,752,1990

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 3230 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: NIIRDN Drugs in Japan (Ethical Drugs). (Yakugyo Jiho Co., Ltd., Tokyo, Japan) Volume(issue)/page/year: -,752,1990

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 260 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: IYKEDH Iyakuhin Kenkyu. Study of Medical Supplies. (Nippon Koteisho Kyokai, 12-15, 2-chome, Shibuya, Shibuya-ku, Tokyo 150, Japan) V.1- 1970- Volume(issue)/page/year: 15,688,1984

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: >3600 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: NIIRDN Drugs in Japan (Ethical Drugs). (Yakugyo Jiho Co., Ltd., Tokyo, Japan) Volume(issue)/page/year: -,752,1990

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 47800 ug/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: NIIRDN Drugs in Japan (Ethical Drugs). (Yakugyo Jiho Co., Ltd., Tokyo, Japan) Volume(issue)/page/year: -,752,1990 ** REPRODUCTIVE DATA **

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 5500 mg/kg

SEX/DURATION :: female 7-17 day(s) after conception

TOXIC EFFECTS :: Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus) Reproductive - Effects on Newborn - viability index (e.g., # alive at day 4 per # born alive)

REFERENCE :: KSRNAM Kiso to Rinsho. Clinical Report. (Yubunsha Co., Ltd., 1-5, Kanda Suda-Cho, Chiyoda-ku, KS Bldg., Tokyo 101, Japan) V.1- 1960- Volume(issue)/page/year: 16,633,1982

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 625 mg/kg

SEX/DURATION :: female 17-21 day(s) after conception

TOXIC EFFECTS :: Reproductive - Effects on Newborn - growth statistics (e.g.%, reduced weight gain)

REFERENCE :: KSRNAM Kiso to Rinsho. Clinical Report. (Yubunsha Co., Ltd., 1-5, Kanda Suda-Cho, Chiyoda-ku, KS Bldg., Tokyo 101, Japan) V.1- 1960- Volume(issue)/page/year: 16,633,1982

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 3250 mg/kg

SEX/DURATION :: female 6-18 day(s) after conception

TOXIC EFFECTS :: Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus)

REFERENCE :: KSRNAM Kiso to Rinsho. Clinical Report. (Yubunsha Co., Ltd., 1-5, Kanda Suda-Cho, Chiyoda-ku, KS Bldg., Tokyo 101, Japan) V.1- 1960- Volume(issue)/page/year: 16,633,1982

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 6500 mg/kg

SEX/DURATION :: female 6-18 day(s) after conception

TOXIC EFFECTS :: Reproductive - Specific Developmental Abnormalities - musculoskeletal system

REFERENCE :: KSRNAM Kiso to Rinsho. Clinical Report. (Yubunsha Co., Ltd., 1-5, Kanda Suda-Cho, Chiyoda-ku, KS Bldg., Tokyo 101, Japan) V.1- 1960- Volume(issue)/page/year: 16,633,1982

Safety Information

[ Personal Protective Equipment ]:
Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter

[ Hazard Codes ]:
C

[ Risk Phrases ]:
R34

[ Safety Phrases ]:
26-27-36/37/39-45

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
2

[ RTECS ]:
DI0360000

[ HS Code ]:
2922199090

Customs

[ HS Code ]: 2922199090

[ Summary ]:
2922199090. other amino-alcohols, other than those containing more than one kind of oxygen function, their ethers and esters; salts thereof. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:30.0%