Desogestrel (DSG) is a synthetic progestin and prodrug of etonogestrel (ENG), derived from testosterone and used in hormonal contraceptives. DSG is primarily used in oral contraceptives, while ENG is primarily used in implants and vaginal rings.
Abbreviation
DSG
References
Names
13-ethyl-11-methylene-18,19-dinor-17α-4- pregnen-20-yn-17-ol
References
CASRN
54024-22-5
References
PubChem CID
40973
IUPHAR/BPS
7065
KEGG Entry Number
DB00304
Wikipedia Entry Name
Desogestrel
ChEBI ID
CHEBI:4453
ChEMBL ID
CHEMBL1533
ChemSpider ID
37400
ATC Code(s)
References
Molecular Formula
C22H30O
References
Molecular Weight
310.473 g/mol
References
Appearance
White, crystalline powder.
Melting Point
228.2-233.6 °F (109-112 °C)
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Solubility
0.5 mg/L water. Freely soluble in 100% ethanol and in dichloromethane; very soluble in methanol; slightly soluble in 96% ethanol and in ethyl acetate; sparingly soluble in hexane.
References
logP
5.6 (Toral et al., Desogestrel USP SDS)
4.27 (Desogestrel USP SDS)
References
Specific Optical Rotation
[α]20D, +53° to -57° in chloroform.
Storage Conditions
Stable at normal conditions.
Side Effects
General progestin side effects: Abnormal uterine bleeding; breast enlargement, pain, or tenderness; unexpected or increased flow of breast milk; hot flashes; loss of sexual desires; dry mouth; unusual thirst; frequent urination; abdominal pain; cramping; nausea; loss of appetite; dizziness; headache; mood changes; insomnia; unusual tiredness or weakness; swelling in ankles or feet; unusual or rapid weight gain; skin rash; acne; loss or gain of hair; brown spots on skin; sudden changes in vision.
Carcinogenicity
No treatment-related tumorigenic effects seen from administration of desogestrel only. Increase in mammary adenocarcinoma in female rats in the high-dose group compared to controls.
Mutagenicity
Not associated with point mutations in the in vitro Ames test and to chromosomal aberrations in a micronucleus test in female rats.
LD50
MRTD
0.0025 mg/kg/day
Progesterone Receptor Activity
Agonist
References
Estrogen Receptor Activity
ERα: Agonist
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Target Pathways
Bioavailability
76% as etonogestrel.
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Elimination Half-Life (t1/2)
30 h (single or multiple doses)
Serum Protein Binding
As etonogestrel: 58% to serum albumin, 38% to SHBG, 3.5% unbound. (Grandi)
32% to SHBG, 66% to albumin, 2% free. (Schindler)
References
Metabolism
CYP3A4, CYP2C9
Excretion
60% excreted via urine, 35% excreted via feces.
Cmax
Tmax
< 2 h from multiple oral administration of 75 μg desogestrel (Grandi)
1.15 h (Schindler)
References
Inhibition of Ovulation
0.06 mg/day
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Transformation of Endometrium
2.5 mg/cycle
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Menstrual Delay
~0.25 (mg/day
References
Lower Progesterone Receptor and Estrogen Receptor activity than etonogestrel.
Glucuronide and sulfate conjugates of desogestrel and some of its metabolites (3β-hydroxydesogestrel, 15β-hydroxydesogestrel) are also formed.
54024-21-4
54048-10-1
70805-85-5
201360-82-9
Prescription
209170
Prescription
021090
Prescription
202689
Prescription
091346