Tranilast

Modify Date: 2024-01-02 09:56:59

Tranilast Structure
Tranilast structure
Common Name Tranilast
CAS Number 53902-12-8 Molecular Weight 327.331
Density 1.3±0.1 g/cm3 Boiling Point 585.5±50.0 °C at 760 mmHg
Molecular Formula C18H17NO5 Melting Point 166-168ºC
MSDS Chinese USA Flash Point 307.9±30.1 °C
Symbol GHS07
GHS07
Signal Word Warning

 Use of Tranilast


Tranilast is an antiallergic agent.Target: Angiotensin ReceptorTranilast has been approved in Japan and South Korea, since 1982, for the treatment of bronchial asthma, with indications for keloids and hypertrophic scar added in 1993. Tranilast is also used to treat asthma, autoimmune diseases, atopic and fibrotic pathologies, and can also inhibit angiogenesis. The antiproliferative properties of tranilast were found that tranilast elicited an inhibitory effect on fibroblast proliferation in vitro and also suppressed collagen production both in vitro and in vivo . Tranilast also reduced the release of chemical mediators from mast cells and suppressed hypersensitivity reactions. [1]Three-week-old C57Bl/10 and mdx mice received tranilast (~300 mg/kg) in their food for 9 weeks, after which fibrosis was assessed through histological analyses, and functional properties of tibialis anterior muscles were assessed in situ and diaphragm muscle strips in vitro. Tranilast administration did not significantly alter the mass of any muscles in control or mdx mice, but it decreased fibrosis in the severely affected diaphragm muscle by 31% compared with untreated mdx mice (P< 0.05) [2].

 Names

Name tranilast
Synonym More Synonyms

 Tranilast Biological Activity

Description Tranilast is an antiallergic agent.Target: Angiotensin ReceptorTranilast has been approved in Japan and South Korea, since 1982, for the treatment of bronchial asthma, with indications for keloids and hypertrophic scar added in 1993. Tranilast is also used to treat asthma, autoimmune diseases, atopic and fibrotic pathologies, and can also inhibit angiogenesis. The antiproliferative properties of tranilast were found that tranilast elicited an inhibitory effect on fibroblast proliferation in vitro and also suppressed collagen production both in vitro and in vivo . Tranilast also reduced the release of chemical mediators from mast cells and suppressed hypersensitivity reactions. [1]Three-week-old C57Bl/10 and mdx mice received tranilast (~300 mg/kg) in their food for 9 weeks, after which fibrosis was assessed through histological analyses, and functional properties of tibialis anterior muscles were assessed in situ and diaphragm muscle strips in vitro. Tranilast administration did not significantly alter the mass of any muscles in control or mdx mice, but it decreased fibrosis in the severely affected diaphragm muscle by 31% compared with untreated mdx mice (P< 0.05) [2].
Related Catalog
References

[1]. Rogosnitzky, M., R. Danks, and E. Kardash, Therapeutic potential of tranilast, an anti-allergy drug, in proliferative disorders. Anticancer Res, 2012. 32(7): p. 2471-8.

[2]. Swiderski, K., et al., Tranilast administration reduces fibrosis and improves fatigue resistance in muscles of mdx dystrophic mice. Fibrogenesis Tissue Repair, 2014. 7(1): p. 1.

[3]. Huang L, et al. Sinomenine-induced histamine release-like anaphylactoid reactions are blocked by tranilast via inhibiting NF-κB signaling. Pharmacol Res. 2017 Aug 31. pii: S1043-6618(17)30796-X.

 Chemical & Physical Properties

Density 1.3±0.1 g/cm3
Boiling Point 585.5±50.0 °C at 760 mmHg
Melting Point 166-168ºC
Molecular Formula C18H17NO5
Molecular Weight 327.331
Flash Point 307.9±30.1 °C
Exact Mass 327.110687
PSA 84.86000
LogP 4.36
Vapour Pressure 0.0±1.7 mmHg at 25°C
Index of Refraction 1.648
Storage condition 2-8°C
Water Solubility DMSO: 18 mg/mL

 Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
DG8731000
CHEMICAL NAME :
Benzoic acid, 2-((3-(3,4-dimethoxyphenyl)-1-oxo-2-propenyl)amino)-
CAS REGISTRY NUMBER :
53902-12-8
LAST UPDATED :
199612
DATA ITEMS CITED :
17
MOLECULAR FORMULA :
C18-H17-N-O5
MOLECULAR WEIGHT :
327.36
WISWESSER LINE NOTATION :
QVR BMV1U1R CO1 DO1

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 :
1100 mg/kg
TOXIC EFFECTS :
Sense Organs and Special Senses (Eye) - lacrimation Behavioral - somnolence (general depressed activity) Lungs, Thorax, or Respiration - respiratory depression
REFERENCE :
OYYAA2 Oyo Yakuri. Pharmacometrics. (Oyo Yakuri Kenkyukai, CPO Box 180, Sendai 980-91, Japan) V.1- 1967- Volume(issue)/page/year: 12,385,1976
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
395 mg/kg
TOXIC EFFECTS :
Behavioral - somnolence (general depressed activity) Lungs, Thorax, or Respiration - respiratory depression Skin and Appendages - dermatitis, other (after systemic exposure)
REFERENCE :
OYYAA2 Oyo Yakuri. Pharmacometrics. (Oyo Yakuri Kenkyukai, CPO Box 180, Sendai 980-91, Japan) V.1- 1967- Volume(issue)/page/year: 12,385,1976
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
3060 mg/kg
TOXIC EFFECTS :
Sense Organs and Special Senses (Eye) - lacrimation Sense Organs and Special Senses (Eye) - ptosis Behavioral - somnolence (general depressed activity)
REFERENCE :
OYYAA2 Oyo Yakuri. Pharmacometrics. (Oyo Yakuri Kenkyukai, CPO Box 180, Sendai 980-91, Japan) V.1- 1967- Volume(issue)/page/year: 12,385,1976
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
680 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
OYYAA2 Oyo Yakuri. Pharmacometrics. (Oyo Yakuri Kenkyukai, CPO Box 180, Sendai 980-91, Japan) V.1- 1967- Volume(issue)/page/year: 19,503,1980
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
385 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
OYYAA2 Oyo Yakuri. Pharmacometrics. (Oyo Yakuri Kenkyukai, CPO Box 180, Sendai 980-91, Japan) V.1- 1967- Volume(issue)/page/year: 19,503,1980
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
2630 mg/kg
TOXIC EFFECTS :
Sense Organs and Special Senses (Eye) - lacrimation Behavioral - somnolence (general depressed activity) Lungs, Thorax, or Respiration - respiratory depression
REFERENCE :
OYYAA2 Oyo Yakuri. Pharmacometrics. (Oyo Yakuri Kenkyukai, CPO Box 180, Sendai 980-91, Japan) V.1- 1967- Volume(issue)/page/year: 12,385,1976
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Mammal - dog
DOSE/DURATION :
660 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: 26,953,1995
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rabbit
DOSE/DURATION :
2625 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
85IQAH "Modern Pharmaceuticals of Japan, IV," Tokyo, Japan Pharmaceutical, Medical and Dental Supply Exporters' Assoc., 1972 Volume(issue)/page/year: -,81,1972 ** OTHER MULTIPLE DOSE TOXICITY DATA **
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
28 gm/kg/5W-C
TOXIC EFFECTS :
Liver - changes in liver weight Kidney, Ureter, Bladder - changes in bladder weight Endocrine - changes in spleen weight
REFERENCE :
OYYAA2 Oyo Yakuri. Pharmacometrics. (Oyo Yakuri Kenkyukai, CPO Box 180, Sendai 980-91, Japan) V.1- 1967- Volume(issue)/page/year: 12,385,1976
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
91 gm/kg/26W-C
TOXIC EFFECTS :
Kidney, Ureter, Bladder - changes in bladder weight Endocrine - changes in adrenal weight Related to Chronic Data - death
REFERENCE :
OYYAA2 Oyo Yakuri. Pharmacometrics. (Oyo Yakuri Kenkyukai, CPO Box 180, Sendai 980-91, Japan) V.1- 1967- Volume(issue)/page/year: 12,407,1976
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Mammal - dog
DOSE/DURATION :
28 gm/kg/15W-I
TOXIC EFFECTS :
Nutritional and Gross Metabolic - weight loss or decreased weight gain
REFERENCE :
85IOAB "Modern Pharmaceuticals of Japan, VII," Tokyo, Japan Pharmaceutical, Medical and Dental Supply Exporters' Association, 1985 Volume(issue)/page/year: -,81,1985
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Mammal - dog
DOSE/DURATION :
65520 mg/kg/1Y-I
TOXIC EFFECTS :
Nutritional and Gross Metabolic - weight loss or decreased weight gain
REFERENCE :
85IOAB "Modern Pharmaceuticals of Japan, VII," Tokyo, Japan Pharmaceutical, Medical and Dental Supply Exporters' Association, 1985 Volume(issue)/page/year: -,81,1985 ** REPRODUCTIVE DATA **
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
1100 mg/kg
SEX/DURATION :
female 7-17 day(s) after conception
TOXIC EFFECTS :
Reproductive - Effects on Newborn - growth statistics (e.g.%, reduced weight gain)
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: 9,161,1978
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
5400 mg/kg
SEX/DURATION :
female 17-22 day(s) after conception lactating female 21 day(s) post-birth
TOXIC EFFECTS :
Reproductive - Effects on Newborn - weaning or lactation index (e.g., # alive at weaning per # alive at day 4)
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: 9,173,1978
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
16200 mg/kg
SEX/DURATION :
female 17-22 day(s) after conception lactating female 21 day(s) post-birth
TOXIC EFFECTS :
Reproductive - Effects on Newborn - viability index (e.g., # alive at day 4 per # born alive)
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: 9,173,1978
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
8500 mg/kg
SEX/DURATION :
male 9 week(s) pre-mating female 2 week(s) pre-mating - 7 day(s) after conception
TOXIC EFFECTS :
Reproductive - Specific Developmental Abnormalities - musculoskeletal system
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: 9,148,1978
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
9750 mg/kg
SEX/DURATION :
female 6-18 day(s) after conception
TOXIC EFFECTS :
Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants)
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: 9,187,1978

 Safety Information

Symbol GHS07
GHS07
Signal Word Warning
Hazard Statements H302
Personal Protective Equipment dust mask type N95 (US);Eyeshields;Gloves
Hazard Codes Xn:Harmful
Risk Phrases R22
Safety Phrases S26-S36
RIDADR NONH for all modes of transport
WGK Germany 3
RTECS DG8731000

 Synthetic Route

~%

Tranilast Structure

Tranilast

CAS#:53902-12-8

Literature: US3940422 A1, ;

 Precursor & DownStream

Precursor  2

DownStream  0

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 Synonyms

2-({(2E)-3-[3,4-bis(methyloxy)phenyl]prop-2-enoyl}amino)benzoic acid
2-{[(2E)-3-(3,4-Dimethoxyphenyl)prop-2-enoyl]amino}benzoic acid
(E)-2-(3-(3,4-dimethoxyphenyl)acrylamido)benzoic acid
benzoic acid, 2-[[(2E)-3-(3,4-dimethoxyphenyl)-1-oxo-2-propenyl]amino]-
2-{[(2E)-3-(3,4-Dimethoxyphenyl)-2-propenoyl]amino}benzoic acid
N-(3,4-Dimethoxycinnamoyl)anthranilic Acid
2-[[3-(3,4-Dimethoxyphenyl)-1-oxo-2-propenyl]amino]benzoic Acid
Tranilast
rizaben
Rizaben,MK 341,Tranpro
MFCD00864787
MK 341
Tranpro
Benzoic acid, 2-[[(2E)-3-(3,4-dimethoxyphenyl)-1-oxo-2-propen-1-yl]amino]-
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