Hydrocortisone-17-butyrate

Iupac Name：[(8S,9S,10R,11S,13S,14S,17R)-11-hydroxy-17-(2-hydroxyacetyl)-10,
13-dimethyl-3-oxo-2,6,7,8,9,11,12,14,15,
16-decahydro-1H-cyclopenta[a]phenanthren-17-yl] butanoate

CAS No.: 13609-67-1

Molecular Weight：432.54974

Modify Date.: 2022-11-22 16:55

Introduction:

ChEBI: Cortisol esterified with butyric acid at the 17-hydroxy group.

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1. Names and Identifiers

1.1 Name: Hydrocortisone-17-butyrate
1.2 Synonyms: (11β)-11,21-Dihydroxy-17-(1-oxobutoxy)pregn-4-ene-3,20-dione 11-beta,17-alpha,21-Trihydroxy-4-pregnene-3,20-dione 17-alpha-butyrate 11β,17,21-trihydroxypregn-4-ene-3,20-dione 17-butyrate 4-Pregnene-11β,21-dihydroxy-17α-butyryloxy-3,20-dione Alfason Bucort Butyric acid, 17-ester with cortisol Cortisol, 17-butyrate Hydrocortisone 17-butyrate Hydrocortisone 17α-butyrate Hydrocortisone butyrate Hydrocortisone butyrate (JP14/USP) Hydrocortisone butyrate [USAN:BAN:JAN] Hydrocortisone-17alpha-butyrate Laticort Locoid Plancol Pregn-4-ene-3,20-dione, 11,21-dihydroxy-17-(1-oxobutoxy)-, (11-beta)- Pregn-4-ene-3,20-dione, 11,21-dihydroxy-17-(1-oxobutoxy)-, (11β)-

1.3 CAS No.: 13609-67-1

1.4 CID: 26133

1.5 EINECS(EC#): 237-093-4

1.6 Molecular Formula: C25H36O6 (isomer)

1.7 Inchi: InChI=1S/C25H36O6/c1-4-5-21(30)31-25(20(29)14-26)11-9-18-17-7-6-15-12-16(27)8-10-23(15,2)22(17)19(28)13-24(18,25)3/h12,17-19,22,26,28H,4-11,13-14H2,1-3H3/t17-,18-,19-,22+,23-,24-,25-/m0/s1

1.8 InChkey: BMCQMVFGOVHVNG-TUFAYURCSA-N

1.9 Canonical Smiles: CCCC(=O)OC1(CCC2C1(CC(C3C2CCC4=CC(=O)CCC34C)O)C)C(=O)CO

1.10 Isomers Smiles: CCCC(=O)O[C@@]1(CC[C@@H]2[C@@]1(C[C@@H]([C@H]3[C@H]2CCC4=CC(=O)CC[C@]34C)O)C)C(=O)CO

2. Properties

2.1 Density: 1.23

2.1 Melting point: 210.0 to 214.0 °C

2.1 Boiling point: 585.6°Cat760mmHg

2.1 Refractive index: 1.564

2.1 Flash Point: 194°C

2.1 Precise Quality: 432.25100

2.1 PSA: 100.90000

2.1 logP: 3.13260

2.1 Appearance: White to Almost white powder to crystal

2.2 Contact Allergens: Hydrocortisone 17-butyrate is a C 17 ester of hydrocorti-sone. It represents the D2 group of corticosteroids, nonC 16 methylated with a C 17 ester: hydrocortisone17-butyrate, hydrocortisone 17-valerate, hydrocortisoneaceponate (17-propionate and 21-acetate), methylpred-nisolone aceponate, and prednicarbate. It is sometimeshydrolyzed in vivo into hydrocortisone, giving allergicreactions to group-A-sensitized people. Hydrocortisone-17-butyrateSupplier

2.3 pKa: 12.98±0.10(Predicted)

3. Use and Manufacturing

3.1 Definition: ChEBI: Cortisol esterified with butyric acid at the 17-hydroxy group.

3.2 Usage: antineoplastic

4. Safety and Handling

4.1 Hazard Declaration: H302+H312+H332

4.1 RIDADR: NONH for all modes of transport

4.1 Caution Statement: P201, P202, P260, P261, P264, P270, P271, P280, P281, P301+P312, P302+P352, P304+P312, P304+P340, P305+P351+P338, P308+P313, P312, P314, P321, P322, P330, P332+P313, P337+P313, P362, P363, P405, P501

4.1 WGK Germany: 2

4.1 RTECS: GM9002000

4.1 Safety: Moderately toxic by subcutaneous and intraperitoneal routes. Experimental teratogenic and reproductive effects. A steroid. When heated to decomposition it emits acrid smoke and fumes. See also HYDROCORTISONE-21-ACETATE; HYDROCORTISONE-17-BUTYRATE-21-PROPIONATE; HYDROCORTISONE-21-PHOSPHATE; HYDROCORTISONE SODIUM SUCCINATE.

4.2 Toxicity

CHEMICAL IDENTIFICATION

RTECS NUMBER :: GM9002000

CHEMICAL NAME :: Cortisol, 17-butyrate

CAS REGISTRY NUMBER :: 13609-67-1

LAST UPDATED :: 199609

DATA ITEMS CITED :: 22

MOLECULAR FORMULA :: C25-H36-O6

MOLECULAR WEIGHT :: 432.61

WISWESSER LINE NOTATION :: L E5 B666 OV MUTJ A1 CQ E1 FV1Q FOV3

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 :: >3 gm/kg

TOXIC EFFECTS :: Nutritional and Gross Metabolic - weight loss or decreased weight gain

REFERENCE :: OYYAA2 Oyo Yakuri. Pharmacometrics. (Oyo Yakuri Kenkyukai, CPO Box 180, Sendai 980-91, Japan) V.1- 1967- Volume(issue)/page/year: 8,991,1974

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

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: >3 gm/kg

TOXIC EFFECTS :: Behavioral - changes in motor activity (specific assay) Gastrointestinal - hypermotility, diarrhea Kidney, Ureter, Bladder - hematuria

REFERENCE :: OYYAA2 Oyo Yakuri. Pharmacometrics. (Oyo Yakuri Kenkyukai, CPO Box 180, Sendai 980-91, Japan) V.1- 1967- Volume(issue)/page/year: 8,991,1974

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

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: >3 gm/kg

TOXIC EFFECTS :: Behavioral - changes in motor activity (specific assay) Gastrointestinal - hypermotility, diarrhea Kidney, Ureter, Bladder - hematuria

REFERENCE :: OYYAA2 Oyo Yakuri. Pharmacometrics. (Oyo Yakuri Kenkyukai, CPO Box 180, Sendai 980-91, Japan) V.1- 1967- Volume(issue)/page/year: 8,991,1974

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

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: >3 gm/kg

TOXIC EFFECTS :: Nutritional and Gross Metabolic - weight loss or decreased weight gain

REFERENCE :: OYYAA2 Oyo Yakuri. Pharmacometrics. (Oyo Yakuri Kenkyukai, CPO Box 180, Sendai 980-91, Japan) V.1- 1967- Volume(issue)/page/year: 8,991,1974

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

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 1550 mg/kg

TOXIC EFFECTS :: Behavioral - somnolence (general depressed activity) Kidney, Ureter, Bladder - hematuria Skin and Appendages - hair

REFERENCE :: OYYAA2 Oyo Yakuri. Pharmacometrics. (Oyo Yakuri Kenkyukai, CPO Box 180, Sendai 980-91, Japan) V.1- 1967- Volume(issue)/page/year: 8,991,1974

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

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 2150 mg/kg

TOXIC EFFECTS :: Sense Organs and Special Senses (Eye) - ptosis Behavioral - changes in motor activity (specific assay) Lungs, Thorax, or Respiration - respiratory depression

REFERENCE :: JTSCDR Journal of Toxicological Sciences. (Japanese Soc. of Toxicological Sciences, 4th Floor, Gakkai Center Bldg., 4-16, Yayoi 2-chome, Bunkyo-ku, Tokyo 113, Japan) V.1- 1976- Volume(issue)/page/year: 6(Suppl 1),1,1981 ** OTHER MULTIPLE DOSE TOXICITY DATA **

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Administration onto the skin

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 87500 mg/kg/35D-C

TOXIC EFFECTS :: Liver - changes in liver weight Endocrine - changes in thymus weight Blood - changes in erythrocyte (RBC) count

REFERENCE :: OYYAA2 Oyo Yakuri. Pharmacometrics. (Oyo Yakuri Kenkyukai, CPO Box 180, Sendai 980-91, Japan) V.1- 1967- Volume(issue)/page/year: 20,225,1980

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Administration onto the skin

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 183 mg/kg/1Y-I

TOXIC EFFECTS :: Blood - changes in serum composition (e.g. TP, bilirubin, cholesterol) Blood - changes in erythrocyte (RBC) count Blood - changes in leukocyte (WBC) count

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: 21,1437,1987

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Administration onto the skin

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 7500 ug/kg/30D-I

TOXIC EFFECTS :: Endocrine - changes in thymus weight Blood - changes in bone marrow (not otherwise specified) Nutritional and Gross Metabolic - weight loss or decreased weight gain

REFERENCE :: JTSCDR Journal of Toxicological Sciences. (Japanese Soc. of Toxicological Sciences, 4th Floor, Gakkai Center Bldg., 4-16, Yayoi 2-chome, Bunkyo-ku, Tokyo 113, Japan) V.1- 1976- Volume(issue)/page/year: 7(Suppl 1),15,1982

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 90 mg/kg/90D-I

TOXIC EFFECTS :: Blood - changes in erythrocyte (RBC) count Skin and Appendages - hair Nutritional and Gross Metabolic - weight loss or decreased 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: 21,1309,1987

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 15 mg/kg/30D-C

TOXIC EFFECTS :: Endocrine - changes in thymus weight Blood - changes in serum composition (e.g. TP, bilirubin, cholesterol) Related to Chronic Data - changes in testicular weight

REFERENCE :: OYYAA2 Oyo Yakuri. Pharmacometrics. (Oyo Yakuri Kenkyukai, CPO Box 180, Sendai 980-91, Japan) V.1- 1967- Volume(issue)/page/year: 8,991,1974

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 91 mg/kg/26W-C

TOXIC EFFECTS :: Lungs, Thorax, or Respiration - changes in lung weight Blood - changes in serum composition (e.g. TP, bilirubin, cholesterol) Related to Chronic Data - changes in testicular weight

REFERENCE :: OYYAA2 Oyo Yakuri. Pharmacometrics. (Oyo Yakuri Kenkyukai, CPO Box 180, Sendai 980-91, Japan) V.1- 1967- Volume(issue)/page/year: 8,991,1974

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 15600 ug/kg/26W-I

TOXIC EFFECTS :: Blood - changes in serum composition (e.g. TP, bilirubin, cholesterol) Blood - changes in leukocyte (WBC) count Blood - changes in platelet count

REFERENCE :: JTSCDR Journal of Toxicological Sciences. (Japanese Soc. of Toxicological Sciences, 4th Floor, Gakkai Center Bldg., 4-16, Yayoi 2-chome, Bunkyo-ku, Tokyo 113, Japan) V.1- 1976- Volume(issue)/page/year: 6(Suppl 1),6,1981

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Administration onto the skin

SPECIES OBSERVED :: Mammal - dog

DOSE/DURATION :: 90 mg/kg/90D-C

TOXIC EFFECTS :: Liver - other changes Endocrine - adrenal cortex hypoplasia Blood - other changes

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: 21,1389,1987 ** REPRODUCTIVE DATA **

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Administration onto the skin

DOSE :: 16500 ug/kg

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

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

REFERENCE :: YACHDS Yakuri to Chiryo. Pharmacology and Therapeutics. (Raifu Saiensu Shuppan K.K., 2-5-13, Yaesu, Chuo-ku, Tokyo 104, Japan) V.1- 1972- Volume(issue)/page/year: 9,3045,1981

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Subcutaneous

DOSE :: 54 mg/kg

SEX/DURATION :: female 9-14 day(s) after conception

TOXIC EFFECTS :: Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants) Reproductive - Effects on Embryo or Fetus - fetal death Reproductive - Effects on Newborn - live birth index (measured after birth)

REFERENCE :: OYYAA2 Oyo Yakuri. Pharmacometrics. (Oyo Yakuri Kenkyukai, CPO Box 180, Sendai 980-91, Japan) V.1- 1967- Volume(issue)/page/year: 8,1035,1974

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Subcutaneous

DOSE :: 1100 ug/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 - Specific Developmental Abnormalities - musculoskeletal system

REFERENCE :: OYYAA2 Oyo Yakuri. Pharmacometrics. (Oyo Yakuri Kenkyukai, CPO Box 180, Sendai 980-91, Japan) V.1- 1967- Volume(issue)/page/year: 21,441,1981

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Subcutaneous

DOSE :: 55 mg/kg

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

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

REFERENCE :: OYYAA2 Oyo Yakuri. Pharmacometrics. (Oyo Yakuri Kenkyukai, CPO Box 180, Sendai 980-91, Japan) V.1- 1967- Volume(issue)/page/year: 20,67,1980

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Subcutaneous

DOSE :: 6 mg/kg

SEX/DURATION :: female 7-12 day(s) after conception

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

REFERENCE :: OYYAA2 Oyo Yakuri. Pharmacometrics. (Oyo Yakuri Kenkyukai, CPO Box 180, Sendai 980-91, Japan) V.1- 1967- Volume(issue)/page/year: 8,1035,1974

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Administration onto the skin

DOSE :: 1300 ug/kg

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

TOXIC EFFECTS :: Reproductive - Fertility - pre-implantation mortality (e.g. reduction in number of implants per female; total number of implants per corpora lutea) Reproductive - Fertility - litter size (e.g. # fetuses per litter; measured before birth)

REFERENCE :: OYYAA2 Oyo Yakuri. Pharmacometrics. (Oyo Yakuri Kenkyukai, CPO Box 180, Sendai 980-91, Japan) V.1- 1967- Volume(issue)/page/year: 33,343,1987

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Subcutaneous

DOSE :: 3250 ug/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) Reproductive - Specific Developmental Abnormalities - craniofacial (including nose and tongue) Reproductive - Specific Developmental Abnormalities - musculoskeletal system

REFERENCE :: OYYAA2 Oyo Yakuri. Pharmacometrics. (Oyo Yakuri Kenkyukai, CPO Box 180, Sendai 980-91, Japan) V.1- 1967- Volume(issue)/page/year: 20,87,1980

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Subcutaneous

DOSE :: 3250 ug/kg

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

TOXIC EFFECTS :: Reproductive - Maternal Effects - uterus, cervix, vagina

REFERENCE :: OYYAA2 Oyo Yakuri. Pharmacometrics. (Oyo Yakuri Kenkyukai, CPO Box 180, Sendai 980-91, Japan) V.1- 1967- Volume(issue)/page/year: 20,87,1980

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5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Reproductive toxicity, Category 2

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word	Warning
Hazard statement(s)	H361 Suspected of damaging fertility or the unborn child
Precautionary statement(s)
Prevention	P201 Obtain special instructions before use. P202 Do not handle until all safety precautions have been read and understood. P280 Wear protective gloves/protective clothing/eye protection/face protection.
Response	P308+P313 IF exposed or concerned: Get medical advice/ attention.
Storage	P405 Store locked up.
Disposal	P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

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6. NMR Spectrum

13C NMR : Predict

1H NMR : Predict

Predict 1H proton NMR

7. Synthesis Route

13609-67-1Total: 3 Synthesis Route

50-23-7 180 Suppliers

13609-67-1 114 Suppliers

Literatures:
US4290962 A1, ;
Yield: null

49757-02-0

13609-67-1 114 Suppliers

Literatures:
Sugai; Okazaki; Akaboshi Synthesis, 1984 , vol. NO. 8, p. 700 - 701
Yield: ~79%

50-23-7 180 Suppliers

43083-12-1 121 Suppliers

13609-67-1 114 Suppliers

6677-99-2 2 Suppliers

Literatures:
Steroids, , vol. 42, # 1 p. 23 - 36
Yield: null

8. Precursor and Product

precursor:

49757-02-0

50-23-7

43083-12-1

9. Other Information

9.0 Merck: 14,4787

9.1 Uses: antineoplastic

9.2 Uses: Hydrocortisone Butyrate is a topical corticosteroid use to treat a variety of dermatological conditions. It acts as an antiinflammatory, antiproliferative and immunosuppresive agent.

9.3 Definition: ChEBI: Cortisol esterified with butyric acid at the 17-hydroxy group.

9.4 Brand name: Locoid (Ferndale); Locoid (Yamanouchi).

9.5 Contact allergens: Hydrocortisone 17-butyrate is a C 17 ester of hydrocorti- sone. It represents the D2 group of corticosteroids, non C 16 methylated with a C 17 ester: hydrocortisone 17-butyrate, hydrocortisone 17-valerate, hydrocortisone aceponate (17-propionate and 21-acetate), methylpred- nisolone aceponate, and prednicarbate. It is sometimes hydrolyzed in vivo into hydrocortisone, giving allergic reactions to group-A-sensitized people.

10. Computational chemical data

Molecular Weight: 432.54974g/mol
Molecular Formula: C₂₅H₃₆O₆
Compound Is Canonicalized: True
XLogP3-AA: null
Exact Mass: 432.25118886
Monoisotopic Mass: 432.25118886
Complexity: 817
Rotatable Bond Count: 6
Hydrogen Bond Donor Count: 2
Hydrogen Bond Acceptor Count: 6
Topological Polar Surface Area: 101
Heavy Atom Count: 31
Defined Atom Stereocenter Count: 7
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Isotope Atom Count: 0
Covalently-Bonded Unit Count: 1
CACTVS Substructure Key Fingerprint: AAADcfB4OAAAAAAAAAAAAAAAAAAAAYAAAAAwYIAAAAAAAGDAAAAAGgAACAAAD1SggAICCAAABgCIAqDSCAIAAAAgAAAACAFAAEgAEBIAAQQCQAAFgAAIAQPIzPDPgAAAAAAAAADAAAYAADAAAYAADAAAAA==

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