Dexamethasone-17-acetate

Modify Date: 2024-01-01 18:41:40

Dexamethasone-17-acetate Structure
Dexamethasone-17-acetate structure
Common Name Dexamethasone-17-acetate
CAS Number 1177-87-3 Molecular Weight 434.498
Density 1.3±0.1 g/cm3 Boiling Point 579.4±50.0 °C at 760 mmHg
Molecular Formula C24H31FO6 Melting Point 238-240 °C(lit.)
MSDS Chinese USA Flash Point 304.2±30.1 °C
Symbol GHS07
GHS07
Signal Word Warning

 Use of Dexamethasone-17-acetate


Dexamethasone acetate is a glucocorticoid receptor agonist.

 Names

Name Dexamethasone-17-acetate
Synonym More Synonyms

 Dexamethasone-17-acetate Biological Activity

Description Dexamethasone acetate is a glucocorticoid receptor agonist.
Related Catalog
Target

Glucocorticoid receptor[1]

In Vitro Dexamethasone regulates several transcription factors, including activator protein-1, nuclear factor-AT, and nuclear factor-kB, leading to the activation and repression of key genes involved in the inflammatory response[1]. Dexamethasone potently inhibits granulocyte-macrophage colony stimulating factor (GM-CSF) release from A549 cells with EC50 of 2.2 nM. Dexamethasone (EC50=36 nM) induces transcription of the β2-receptor is found to correlate with glucocorticoid receptor (GR) DNA binding and occurred at 10-100 fold higher concentrations than the inhibition of GM-CSF release. Dexamethasone (IC50=0.5 nM) inhibits a 3×κB (NF-κB, IκBα, and I-κBβ), which is associated with inhibition of GM-CSF release[2].
In Vivo It has previously been reported that treatment with Dexamethasone at a dose of 2×5 mg/kg efficiently inhibits lipopolysaccharide (LPS)-induced inflammation. In our experimental system, treatment with a single dose of Dexamethasone 10 mg/kg (i.p.) significantly decreases recruitment of granulocytes as well as spontaneous production of oxygen radicals compared with animals expose to LPS and injected with solvent alone (saline). The effects are statistically significant when administered both 1 h before and 1 h after inhalation of LPS. The number of granulocytes in BALF decreased to levels comparable to healthy animals (given an aerosol of water)[3]. Rats treated with Dexamethasone consume less food and weighed less than control rats. Treated rats also weigh less than pair-fed animals though their food intake is similar. Five days of Dexamethasone injection result in a significant increase in both the liver mass (+42%) and the liver to body weight ratio (+65%). The wet weight of gastrocnemius muscle decreases 20% after 5 days of treatment, but it remains unaffected relative to body weight (g/100 g body weight), indicating that muscle weight loss paralleled body weight loss[4].
Animal Admin Mice[3] Female C57Bl/6JBom mice (age 10-12 weeks) are used in all experiments. Dexamethasone is administered as a single injection of 1 or 10 mg/kg. Dexamethasone is dissolved in saline and 400 μL are injected intraperitoneally, either 1 h before or 1 h after LPS exposure. In one experiment, N-acetylcysteine (NAC) (100 and 500 mg/kg) is injected successively every 4•5 h, starting 1 h before challenge (five injections in total). A control group of LPS-exposed animals are injected intraperitoneally with solvent alone (saline). Intratracheal administration is performed by instillation of 100 μL NAC (50, 100 or 500 mg/kg) or Dexamethasone (10 mg/kg) into the lungs of mice anaesthetized with 15 mg/kg Rapinovet (i.v.). Rats[4] Male Sprague-Dawley rats are used.Dexamethasone-treated rats are injected intraperitoneally once daily with Dexamethasone (1.5 mg/kg body weight) for 5 days and are allowed to feed ad libitum. The Dexamethasone dose (1.5 mg/kg/day) and the duration of treatment (5 days) are specifically chosen as this treatment induced a reproducible and marked catabolic state. Control rats received no treatment and are fed ad libitum. In order to take into account the decrease in food intake induced by Dexamethasone treatment, a third group of pair-fed rats are used. These rats are provided with the same amount of food as Dexamethasone-injected rats and are treated with a daily isovolumic intraperitoneal injection of NaCl (0.9%) for 5 days. After the final injection of Dexamethasone or NaCl, the animals are fasted overnight prior to being killed by decapitation.
References

[1]. LaLone CA, et al. Effects of a glucocorticoid receptor agonist, Dexamethasone, on fathead minnow reproduction, growth, and development. Environ Toxicol Chem. 2012 Mar;31(3):611-22.

[2]. Adcock IM, et al. Ligand-induced differentiation of glucocorticoid receptor (GR) trans-repression and transactivation: preferential targetting of NF-kappaB and lack of I-kappaB involvement. Br J Pharmacol. 1999 Jun;127(4):1003-11

[3]. Rocksén D, et al. Differential anti-inflammatory and anti-oxidative effects of Dexamethasone and N-acetylcysteine in endotoxin-induced lung inflammation. Clin Exp Immunol. 2000 Nov;122(2):249-56

[4]. Roussel D, et al. Dexamethasone treatment specifically increases the basal proton conductance of rat liver mitochondria. FEBS Lett. 2003 Apr 24;541(1-3):75-9.

 Chemical & Physical Properties

Density 1.3±0.1 g/cm3
Boiling Point 579.4±50.0 °C at 760 mmHg
Melting Point 238-240 °C(lit.)
Molecular Formula C24H31FO6
Molecular Weight 434.498
Flash Point 304.2±30.1 °C
Exact Mass 434.210480
PSA 100.90000
LogP 2.96
Vapour Pressure 0.0±3.6 mmHg at 25°C
Index of Refraction 1.571
Storage condition 2-8°C

 Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
TU4050000
CHEMICAL NAME :
Pregna-1,4-diene-3,20-dione, 9-fluoro-11-beta,17,21-trihydroxy-16-alpha-methyl-, acetate
CAS REGISTRY NUMBER :
1177-87-3
LAST UPDATED :
199701
DATA ITEMS CITED :
12
MOLECULAR FORMULA :
C24-H31-F-O6
MOLECULAR WEIGHT :
434.55
WISWESSER LINE NOTATION :
L E5 B666 OV AHTTT&J A1 BF CQ E1 FV1OV1 FQ G1

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
1 mg/kg
SEX/DURATION :
female 15-19 day(s) after conception
TOXIC EFFECTS :
Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants) Reproductive - Fertility - abortion
REFERENCE :
FESTAS Fertility and Sterility. (American Fertility Soc., 608 13th Ave. S, Birmingham, AL 35282) V.1- 1950- Volume(issue)/page/year: 22,735,1971
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Subcutaneous
DOSE :
1200 ug/kg
SEX/DURATION :
female 12-13 day(s) after conception
TOXIC EFFECTS :
Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus) Reproductive - Specific Developmental Abnormalities - musculoskeletal system
REFERENCE :
TJADAB Teratology, The International Journal of Abnormal Development. (Alan R. Liss, Inc., 41 E. 11th St., New York, NY 10003) V.1- 1968- Volume(issue)/page/year: 23,15,1981
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Subcutaneous
DOSE :
1200 ug/kg
SEX/DURATION :
female 12-13 day(s) after conception
TOXIC EFFECTS :
Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus) Reproductive - Specific Developmental Abnormalities - body wall
REFERENCE :
DPTHDL Developmental Pharmacology and Therapeutics. (S. Karger Pub., Inc., 79 Fifth Ave., New York, NY 10003) V.1- 1980- Volume(issue)/page/year: 4,89,1982
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Subcutaneous
DOSE :
2400 ug/kg
SEX/DURATION :
female 12-13 day(s) after conception
TOXIC EFFECTS :
Reproductive - Specific Developmental Abnormalities - craniofacial (including nose and tongue)
REFERENCE :
DPTHDL Developmental Pharmacology and Therapeutics. (S. Karger Pub., Inc., 79 Fifth Ave., New York, NY 10003) V.1- 1980- Volume(issue)/page/year: 4,89,1982
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Subcutaneous
DOSE :
12800 ug/kg
SEX/DURATION :
female 9-12 day(s) after conception
TOXIC EFFECTS :
Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants) Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus)
REFERENCE :
SEIJBO Senten Ijo. Congenital Anomalies. (Nippon Senten Ijo Gakkai, c/o Kinki Daigaku Igakubu Kaibagaku Kyoshitsu, 380 Nishiyama, Sayama-cho, Mirami-Kawachi-gun, Osaka-fu, Japan) V.1-26, 1960-86. For publisher information, see CGANE7. Volume(issue)/page/year: 13,245,1973
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Subcutaneous
DOSE :
12800 ug/kg
SEX/DURATION :
female 11-14 day(s) after conception
TOXIC EFFECTS :
Reproductive - Specific Developmental Abnormalities - craniofacial (including nose and tongue)
REFERENCE :
SEIJBO Senten Ijo. Congenital Anomalies. (Nippon Senten Ijo Gakkai, c/o Kinki Daigaku Igakubu Kaibagaku Kyoshitsu, 380 Nishiyama, Sayama-cho, Mirami-Kawachi-gun, Osaka-fu, Japan) V.1-26, 1960-86. For publisher information, see CGANE7. Volume(issue)/page/year: 13,245,1973
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intravenous
DOSE :
128 mg/kg
SEX/DURATION :
female 11-14 day(s) after conception
TOXIC EFFECTS :
Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants) Reproductive - Specific Developmental Abnormalities - craniofacial (including nose and tongue)
REFERENCE :
SEIJBO Senten Ijo. Congenital Anomalies. (Nippon Senten Ijo Gakkai, c/o Kinki Daigaku Igakubu Kaibagaku Kyoshitsu, 380 Nishiyama, Sayama-cho, Mirami-Kawachi-gun, Osaka-fu, Japan) V.1-26, 1960-86. For publisher information, see CGANE7. Volume(issue)/page/year: 13,245,1973
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Ocular
DOSE :
1200 ug/kg
SEX/DURATION :
female 10-13 day(s) after conception
TOXIC EFFECTS :
Reproductive - Specific Developmental Abnormalities - craniofacial (including nose and tongue)
REFERENCE :
TJADAB Teratology, The International Journal of Abnormal Development. (Alan R. Liss, Inc., 41 E. 11th St., New York, NY 10003) V.1- 1968- Volume(issue)/page/year: 16,175,1977
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Ocular
DOSE :
6 mg/kg
SEX/DURATION :
female 10-13 day(s) after conception
TOXIC EFFECTS :
Reproductive - Specific Developmental Abnormalities - urogenital system
REFERENCE :
TJADAB Teratology, The International Journal of Abnormal Development. (Alan R. Liss, Inc., 41 E. 11th St., New York, NY 10003) V.1- 1968- Volume(issue)/page/year: 16,175,1977
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Subcutaneous
DOSE :
6 mg/kg
SEX/DURATION :
female 24-26 day(s) after conception
TOXIC EFFECTS :
Reproductive - Effects on Newborn - biochemical and metabolic
REFERENCE :
BCPCA6 Biochemical Pharmacology. (Pergamon Press Inc., Maxwell House, Fairview Park, Elmsford, NY 10523) V.1- 1958- Volume(issue)/page/year: 27,1007,1978
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Subcutaneous
DOSE :
9 mg/kg
SEX/DURATION :
female 5-7 day(s) after conception
TOXIC EFFECTS :
Reproductive - Fertility - other measures of fertility
REFERENCE :
BIREBV Biology of Reproduction. (Soc. for the Study of Reproduction, 309 W. Clark St., Champaign, IL 61820) V.1- 1969- Volume(issue)/page/year: 30,544,1984

 Safety Information

Symbol GHS07
GHS07
Signal Word Warning
Hazard Statements H317
Precautionary Statements P280
Personal Protective Equipment dust mask type N95 (US);Eyeshields;Faceshields;Gloves
Hazard Codes Xi:Irritant
Risk Phrases R43
Safety Phrases S36/37
RIDADR 2811.0
WGK Germany 3
RTECS TU4050000
Hazard Class 6.1
HS Code 2937229000

 Synthetic Route

 Customs

HS Code 2937229000

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 Synonyms

9α-Fluoro-11β,17α,21-trihydroxy-16α-methyl-1,4-pregnadiene-3,20-dione 21-Acetate
Pregna-1,4-diene-3,20-dione, 9-fluoro-11β,17,21-trihydroxy-16α-methyl-, 21-acetate (8CI)
(11β,16α)-9-Fluoro-11,17-dihydroxy-16-methyl-3,20-dioxopregna-1,4-dien-21-yl acetate
Pregna-1,4-diene-3,20-dione, 21-(acetyloxy)-9-fluoro-11,17-dihydroxy-16-methyl-, (11β,16α)-
MFCD00027407
(11b,16a)-9-Fluoro-11,17,21-trihydroxy-16-methylpregna-1,4-diene-3,20-dione 21-Acetate
Dexamethasone acetate
EINECS 214-646-8
DEXAMETHASONE 21-ACETATE
Dexamethasone (acetate)