Turosteride
Turosteride
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Systematic (IUPAC) name |
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(4aR,4bS,6aS,7S,9aS,9bS,11aR)-1,4a,6a-trimethyl-2-oxo-N-(propan-2-yl)-N-(propan-2-ylcarbamoyl)hexadecahydro-1H-indeno[5,4-f]quinoline-7-carboxamide |
Clinical data |
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Oral |
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Identifiers |
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137099-09-3 |
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None |
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PubChem |
CID 65986 |
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ChemSpider |
59380 |
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UNII |
LU1LTK666W Y |
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Synonyms |
1-(4-methyl-3-oxo-4-aza-5-alpha-androstane-17-beta-carbonyl)-1,3- diisopropylurea |
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Chemical data |
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Formula |
C27H45N3O3 |
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459.66 g/mol |
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SMILES
- O=C(NC(C)C)N(C(=O)[C@@H]2[C@]1(CC[C@H]3[C@H]([C@@H]1CC2)CC[C@H]4N(C(=O)CC[C@]34C)C)C)C(C)C
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InChI=1S/C27H45N3O3/c1-16(2)28-25(33)30(17(3)4)24(32)21-10-9-19-18-8-11-22-27(6,15-13-23(31)29(22)7)20(18)12-14-26(19,21)5/h16-22H,8-15H2,1-7H3,(H,28,33)/t18-,19-,20-,21+,22+,26-,27+/m0/s1
Key:WMPQMBUXZHMEFZ-YJPJVVPASA-N
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Turosteride (FCE-26,073) is a selective inhibitor of the enzyme 5α-reductase which was under investigation by GlaxoSmithKline for the treatment of benign prostatic hyperplasia (BPH), but was never marketed.[1][2][3] Similarly to finasteride, turosteride is selective for the type II isoform of 5α-redcutase, with about 15-fold selectivity for it over type I isoform of the enzyme.[4][5] In animal studies it has been shown to inhibit prostate size and retard tumor growth.[2][3][6][7] It may also be useful for the treatment of acne and hair loss.[8][9][10]
See also
References
- ↑ David J. Triggle (1996). Dictionary of Pharmacological Agents. Boca Raton: Chapman & Hall/CRC. ISBN 0-412-46630-9.
- ↑ 2.0 2.1 di Salle E, Giudici D, Briatico G, Ornati G, Panzeri A (November 1993). "Hormonal effects of turosteride, a 5 alpha-reductase inhibitor, in the rat". The Journal of Steroid Biochemistry and Molecular Biology 46 (5): 549–55. doi:10.1016/0960-0760(93)90181-U. PMID 8240976.
- ↑ 3.0 3.1 Di Salle E, Briatico G, Giudici D, Ornati G, Panzeri A (February 1994). "Endocrine properties of the testosterone 5 alpha-reductase inhibitor turosteride (FCE 26073)". The Journal of Steroid Biochemistry and Molecular Biology 48 (2-3): 241–8. doi:10.1016/0960-0760(94)90151-1. PMID 8142301.
- ↑ Iehlé C, Délos S, Guirou O, Tate R, Raynaud JP, Martin PM (September 1995). "Human prostatic steroid 5 alpha-reductase isoforms--a comparative study of selective inhibitors". The Journal of Steroid Biochemistry and Molecular Biology 54 (5-6): 273–9. doi:10.1016/0960-0760(95)00134-L. PMID 7577710.
- ↑ Seiffert K, Seltmann H, Fritsch M, Zouboulis CC (February 2007). "Inhibition of 5alpha-reductase activity in SZ95 sebocytes and HaCaT keratinocytes in vitro". Hormone and Metabolic Research = Hormon- Und Stoffwechselforschung = Hormones Et Métabolisme 39 (2): 141–8. doi:10.1055/s-2007-961814. PMID 17326010.
- ↑ Zaccheo T, Giudici D, di Salle E (February 1997). "Effect of turosteride, a 5 alpha-reductase inhibitor, on the Dunning R3327 rat prostatic carcinoma". The Prostate 30 (2): 85–91. doi:10.1002/(SICI)1097-0045(19970201)30:2<85::AID-PROS3>3.0.CO;2-J. PMID 9051146.
- ↑ Zaccheo T, Giudici D, di Salle E (June 1998). "Effect of early treatment of prostate cancer with the 5alpha-reductase inhibitor turosteride in Dunning R3327 prostatic carcinoma in rats". The Prostate 35 (4): 237–42. doi:10.1002/(SICI)1097-0045(19980601)35:4<237::AID-PROS1>3.0.CO;2-D. PMID 9609545.
- ↑ Rawlings, Anthony V.; Webster, Guy F. (2007). Acne and its therapy. New York: Informa Healthcare USA. ISBN 0-8247-2971-4.
- ↑ "Hairloss Treatment: Turosteride".
- ↑ "Hair Loss Drugs - Turosteride - competitive and specific inhibitor of Type II 5a-reductase. - Database of Drugs for Hair Loss".
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| 5α-reductase inhibitors | |
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| Alpha blockers (α1) | |
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| Herbals | |
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| Other | |
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| Description |
- Anatomy
- Physiology
- Development
- sex determination and differentiation
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| Disease |
- Infections
- Congenital
- Neoplasms and cancer
- male
- female
- gonadal
- germ cell
- Other
- Symptoms and signs
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| Treatment |
- Procedures
- Drugs
- benign prostatic hypertrophy
- erectile dysfunction and premature ejaculation
- sexual dysfunction
- infection
- hormones
- androgens
- estrogens
- progestogens
- GnRH
- prolactin
- Assisted reproduction
- Birth control
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Other dermatological preparations ( D11) |
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| Medicated shampoos | |
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| Other dermatologicals | |
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| Description |
- Anatomy
- Physiology
- Development
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| Disease |
- Infections
- Vesiculobullous
- Dermatitis and eczema
- Papulosquamous
- Urticaria and erythema
- Radiation-related
- Pigmentation
- Mucinoses
- Keratosis, ulcer, atrophy, and necrobiosis
- Vasculitis
- Fat
- Neutrophilic and eosinophilic
- Congenital
- Neoplasms and cancer
- nevi and melanomas
- epidermis
- dermis
- Symptoms and signs
- Terminology
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| Treatment |
- Procedures
- Drugs
- antibiotics
- disinfectants
- emollients and protectives
- itch
- psoriasis
- other
- Wound and ulcer
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| Description |
- Anatomy
- Physiology
- Development
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| Disease |
- Congenital
- Neoplasms and cancer
- Other
- Symptoms and signs
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| Treatment | |
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| Receptor | |
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| Enzyme | |
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| Others |
- Indirect: Antigonadotropins (e.g., estrogens, progestogens, prolactin)
- GnRH agonists (e,g, GnRH, leuprorelin)
- GnRH antagonists (e.g., cetrorelix)
- Gonadotropins (e.g., FSH, hCG, LH)
- Kisspeptin
- Plasma proteins (ABP, albumin, SHBG)
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| See also: Estrogenics • Glucocorticoidics • Mineralocorticoidics • Progestogenics |
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