코르티손-21-아세트산

코르티손-21-아세트산
코르티손-21-아세트산 구조식 이미지
카스 번호:
50-04-4
한글명:
코르티손-21-아세트산
동의어(한글):
코르티손아세테이트;코르티손-21-아세트산;코르티손
상품명:
Cortisone acetate
동의어(영문):
artriona;cortelan;cortisyl;ricortex;NSC 49420;cortistab;biocortacetate;cortoneacetate;irisoneacetate;cortogenacetate
CBNumber:
CB9277612
분자식:
C23H30O6
포뮬러 무게:
402.48
MOL 파일:
50-04-4.mol
MSDS 파일:
SDS

코르티손-21-아세트산 속성

녹는점
237-240 °C(lit.)
끓는 점
577.3±50.0 °C(Predicted)
알파
D25 +164° (c = 0.5 in acetone); D25 +208 to +217° (dioxane)
밀도
1.26±0.1 g/cm3(Predicted)
굴절률
212 ° (C=1, MeOH)
저장 조건
2-8°C
용해도
물에 거의 녹지 않으며, 염화메틸렌에 잘 녹고, 디옥산에 녹고, 아세톤에는 조금 녹고, 에탄올(96%)과 메탄올에는 약간 녹습니다.
산도 계수 (pKa)
12.32±0.60(Predicted)
색상
흰색에서 황백색까지
수용성
19mg/L(25℃)
Merck
14,2539
BRN
2067543
안정성
안정적인. 강한 산화제와 호환되지 않습니다.
CAS 데이터베이스
50-04-4(CAS DataBase Reference)
EPA
Cortisone acetate (50-04-4)
안전
  • 위험 및 안전 성명
  • 위험 및 사전주의 사항 (GHS)
안전지침서 22-36/37-24/25
WGK 독일 3
RTECS 번호 GM9140000
HS 번호 32041200
그림문자(GHS): GHS hazard pictograms
신호 어: Warning
유해·위험 문구:
암호 유해·위험 문구 위험 등급 범주 신호 어 그림 문자 P- 코드
H361 태아 또는 생식능력에 손상을 일으킬 것으로 의심됨 생식독성 물질 구분 2 경고 P201, P202, P281, P308+P313, P405,P501
H373 장기간 또는 반복 노출되면 장기(또는, 영향을 받은 알려진 모든 장기를 명시)에 손상을 일으킬 수 있음 특정 표적장기 독성 - 반복 노출 구분 2 경고 P260, P314, P501
예방조치문구:
P201 사용 전 취급 설명서를 확보하시오.
P202 모든 안전 조치 문구를 읽고 이해하기 전에는 취급하지 마시오.
P260 분진·흄·가스·미스트·증기·...·스프레이를 흡입하지 마시오.
P281 요구되는 개인 보호구를 착용하시오
P308+P313 노출 또는 접촉이 우려되면 의학적인 조치· 조언를 구하시오.
P314 불편함을 느끼면 의학적인 조치·조언을 구하시오.
P405 밀봉하여 저장하시오.
P501 ...에 내용물 / 용기를 폐기 하시오.
NFPA 704
0
3 0

코르티손-21-아세트산 C화학적 특성, 용도, 생산

개요

Cortisone acetate is a synthetic glucocorticoid with anti-inflammatory properties. It decreases the size of Bacillus Calmette-Guérin (BCG) vaccine-induced dermal lesions and tuberculin reactions in rabbits when administered at 2 mg/kg on alternate days over the course of 46 days. It also reduces the number and percentage of activated lesion-infiltrating mononuclear cells and decreases the amount of caseous necrosis and ulceration. Cortisone acetate (2.5 mg/kg per day, s.c.) slows tissue regeneration in a rabbit model of wound healing. It also decreases the number of dexamethasone binding sites on isolated human lymphocytes by 30%. Formulations containing cortisone acetate have been used to relieve inflammation, pruritic manifestations of corticosteroid-responsive dermatoses, and in the treatment of immune and allergic disorders.

화학적 성질

White needle crystal or crystalline powder (acetone), odorless. Stable in the air. Mp239- 241°C, specific rotation [α]20D+164°(0.5%, acetone), [α]23D+169°(chloroform), [α]25D+208°-+217°(dioxane), The ethanol solution of this product has a maximum absorption at a wavelength of 240nm. Soluble in chloroform (1:4), soluble in acetone (1:75), slightly soluble in ethanol and ether, and hardly soluble in water. This product dissolves in sulfuric acid and turns yellow without fluorescence (different from hydrocortisone acetate).

용도

Cortisone Acetate (Hydrocortisone Acetate EP Impurity D) is a glucocorticoid. Cortisone Acetate is an antiinflammatory agent. Cortisone Acetate is bioavailable and readily converted to the therapeutically active form, Hydrocotisone.

제조 방법

Cortisone acetate is prepared from dehydropregnenolone by epoxidation, Wolff's oxidation, mycoxidation, chromic acid oxidation, hydrogen bromide ring-opening, Raney's nickel-catalyzed debromination, iodination, and acetyloxy substitution.

일반 설명

Cortisone acetate, 21-(acetyloxy)-17-hydroxypregn-4-ene-3,11,20-trione, is the 21-acetate of naturally occurring cortisone with good systemicanti-inflammatory activity and low-to-moderate salt-retentionactivity after its in vivo conversion to hydrocortisoneacetate. This conversion is mediated by 11β-hydroxysteroiddehydrogenase. It is used for the entire spectrum of uses discussedpreviously under the heading, “Therapeutic Uses ofAdrenal Cortex Hormones”—collagen diseases, Addisondisease, severe shock, allergic conditions, chronic lymphocyticleukemia, and many other indications. Cortisone acetateis relatively ineffective topically, mainly because itmust be reduced in vivo to hydrocortisone. Its plasma halflifeis only about 30 minutes, compared with 90 minutes to3 hours for hydrocortisone.

Purification Methods

Crystallise -1cortisone-21-acetate from acetone or CHCl3. The UV has 15,800 M-1cm at 238nm in dioxane. [Sarett J Biol Chem 162 601 1946, Beilstein 8 III 4058, 5 IV 3481.]

참고 문헌

1. Cortisone acetate in skin disease; local effect in the skin from topical application and local injection. DOI:10.1001/ARCHDERM.1952.01530210056007
2. McCue, R.E., Dannenberg, A.M., Jr., Huguchi, S., et al. The effect of cortisone on the accumulation, activation, and necrosis of macrophages in tuberculous lesions. Inflammation 3(2), 159-176 (1978). DOI:10.1007/BF00910737
3. Joseph, J., and Tydd, M. The effects of cortisone acetate on tissue regeneration in the rabbit’s ear. J. Anat. 115(Pt. 3), 445-460 (1973).
4. Schlechte, J.A., Ginsberg, B.H., and Sherman, B.M. Regulation of the glucocorticoid receptor in human lymphocytes. J. Steroid Biochem. 16(1), 69-74 (1982). DOI:10.1016/0022-4731(82)90145-5
5. Sittig's Pharmaceutical Manufacturing Encyclopedia
6. Textbook of organic medicinal and pharmaceutical chemistry. DOI:10.1002/jps.3030451120
7. Purification of Laboratory Chemicals DOI:10.5860/choice.50-6768

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