Megestrol Acetate - ≥96%(HPLC) , Progesterone receptor agonist, CAS No.595-33-5, Progesterone receptor agonist

CAS: 595-33-5 Cat. No.: M157891 Molecular Weight: 384.52 Beilstein Registry Number: 8(4)2431 EC Number: 209-864-5

GRADE & PURITY ≥96%(HPLC)

Synonyms

6-Methyl-delta(sup 4,6)-pregnadien-17-alpha-ol-3,20-dione acetate | 6-Methyl-delta(sup 4,6)-pregnadien-17alpha-ol-3,20-dione acetate | Prestwick0_000956 | 6-Methyl-6-dehydro-17.alpha.-acetylprogesterone | HMS3714P14 | Maygace | RQZAXGRLVPAYTJ-GQFGMJRRSA-N

Storage

Room temperature

Shipped In

Normal

Specifications

Synonyms

6-Methyl-delta(sup 4, 6)-pregnadien-17-alpha-ol-3, 20-dione acetate | 6-Methyl-delta(sup 4, 6)-pregnadien-17alpha-ol-3, 20-dione acetate | Prestwick0_000956 | 6-Methyl-6-dehydro-17.alpha.-acetylprogesterone | HMS3714P14 | Maygace | RQZAXGRLVPAYTJ-GQFGMJRRSA-N

Specifications & Purity

≥96%(HPLC)

Biochemical and Physiological Mechanisms

Synthetic progesterone analog. Dose-dependently inhibits growth of HepG2 cells (IC50= 260 μM)in vitroandin vivoand reduces tumor volume. High dosages improve weight gain in tumor-bearing nude mice. Orally bioavailable.

Storage

Room temperature

Shipped In

Normal

Action Type

AGONIST

Mechanism of action

Progesterone receptor agonist

Purity

≥96%(HPLC)

Names and Identifiers

• Pubchem Sid: 488181406
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/488181406
• Canonical Smiles: CC1=CC2C(CCC3(C2CCC3(C(=O)C)OC(=O)C)C)C4(C1=CC(=O)CC4)C
• IUPAC Name: [(8R,9S,10R,13S,14S,17R)-17-acetyl-6,10,13-trimethyl-3-oxo-2,8,9,11,12,14,15,16-octahydro-1H-cyclopenta[a]phenanthren-17-yl] acetate
• InChIKey: RQZAXGRLVPAYTJ-GQFGMJRRSA-N
• INCHI: 1S/C24H32O4/c1-14-12-18-19(22(4)9-6-17(27)13-21(14)22)7-10-23(5)20(18)8-11-24(23,15(2)25)28-16(3)26/h12-13,18-20H,6-11H2,1-5H3/t18-,19+,20+,22-,23+,24+/m1/s1
• Isomeric SMILES: CC1=C[C@@H]2[C@H](CC[C@]3([C@H]2CC[C@@]3(C(=O)C)OC(=O)C)C)[C@@]4(C1=CC(=O)CC4)C
• RTECS: TU4075000
• Molecular Weight: 384.52
• Beilstein: 8(4)2431
• Reaxy-Rn: 3489305
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=3489305&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Lipids and lipid-like molecules
    • Class Steroids and steroid derivatives
      • Subclass Pregnane steroids

• Kingdom: Organic compounds
• Superclass: Lipids and lipid-like molecules
• Class: Steroids and steroid derivatives
• Subclass: Pregnane steroids
• Intermediate Tree Nodes: Not available
• Direct Parent: Gluco/mineralocorticoids, progestogins and derivatives
• Alternative Parents: Steroid esters 20-oxosteroids 3-oxosteroids Cyclohexenones Alpha-acyloxy ketones Carboxylic acid esters Monocarboxylic acids and derivatives Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aliphatic homopolycyclic compounds
• Substituents: Progestogin-skeleton - 20-oxosteroid - Steroid ester - 3-oxosteroid - Oxosteroid - Cyclohexenone - Alpha-acyloxy ketone - Ketone - Carboxylic acid ester - Cyclic ketone - Monocarboxylic acid or derivatives - Carboxylic acid derivative - Hydrocarbon derivative - Organic oxygen compound - Organooxygen compound - Organic oxide - Carbonyl group - Aliphatic homopolycyclic compound
• Description: This compound belongs to the class of organic compounds known as gluco/mineralocorticoids, progestogins and derivatives. These are steroids with a structure based on a hydroxylated prostane moiety.
• External Descriptors: C21 steroids (gluco/mineralocorticoids, progestogins) and derivatives

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Associated Targets(Human)

NR3C1 Tclin Glucocorticoid receptor (2 Activities)

Discover Target: NR3C1

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

PDE5A Tclin Phosphodiesterase 5A (5113 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

EGFR Tclin Epidermal growth factor receptor erbB1 (33727 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

F2 Tclin Thrombin (11687 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CA2 Tclin Carbonic anhydrase II (17698 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ESR1 Tclin Estrogen receptor alpha (17718 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

HMGCR Tclin HMG-CoA reductase (2475 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

NR3C1 Tclin Glucocorticoid receptor (14987 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

INSR Tclin Insulin receptor (5558 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

PGR Tclin Progesterone receptor (8562 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ADRB2 Tclin Beta-2 adrenergic receptor (11824 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CHRM2 Tclin Muscarinic acetylcholine receptor M2 (10671 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ADRB1 Tclin Beta-1 adrenergic receptor (6630 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

HTR1A Tclin Serotonin 1a (5-HT1a) receptor (14969 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ADRA2A Tclin Alpha-2a adrenergic receptor (9450 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

AR Tclin Androgen Receptor (11781 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CHRM1 Tclin Muscarinic acetylcholine receptor M1 (12690 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ACE Tclin Angiotensin-converting enzyme (1423 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

DRD2 Tclin Dopamine D2 receptor (23596 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

GABRA1 Tclin GABA receptor alpha-1 subunit (399 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

MAOA Tclin Monoamine oxidase A (11911 Activities)

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CNR1 Tclin Cannabinoid CB1 receptor (20913 Activities)

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DRD1 Tclin Dopamine D1 receptor (9720 Activities)

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DRD4 Tchem Dopamine D4 receptor (7907 Activities)

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ACHE Tclin Acetylcholinesterase (18204 Activities)

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PTGS1 Tclin Cyclooxygenase-1 (9233 Activities)

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SLC6A2 Tclin Norepinephrine transporter (10102 Activities)

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HRH2 Tclin Histamine H2 receptor (5428 Activities)

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ADRA1D Tclin Alpha-1d adrenergic receptor (4171 Activities)

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MAOB Tclin Monoamine oxidase B (8835 Activities)

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HTR1B Tclin Serotonin 1b (5-HT1b) receptor (2801 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

HTR2A Tclin Serotonin 2a (5-HT2a) receptor (14758 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

HTR2C Tclin Serotonin 2c (5-HT2c) receptor (11471 Activities)

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ADORA1 Tclin Adenosine A1 receptor (17603 Activities)

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CALCR Tclin Calcitonin receptor (2215 Activities)

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SLC6A4 Tclin Serotonin transporter (12625 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ADRA1A Tclin Alpha-1a adrenergic receptor (8359 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

PTGS2 Tclin Cyclooxygenase-2 (13999 Activities)

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HRH1 Tclin Histamine H1 receptor (7573 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ADRA1B Tclin Alpha-1b adrenergic receptor (2912 Activities)

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OPRM1 Tclin Mu opioid receptor (19785 Activities)

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DRD3 Tclin Dopamine D3 receptor (14368 Activities)

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AVPR1A Tclin Vasopressin V1a receptor (5412 Activities)

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OPRD1 Tclin Delta opioid receptor (15096 Activities)

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OPRK1 Tclin Kappa opioid receptor (16155 Activities)

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SLC6A3 Tclin Dopamine transporter (10535 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

KCNH2 Tclin HERG (29587 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

HTR4 Tclin Serotonin 4 (5-HT4) receptor (2068 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

PDE3A Tclin Phosphodiesterase 3A (3309 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ESR2 Tclin Estrogen receptor beta (9272 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CYSLTR1 Tclin Cysteinyl leukotriene receptor 1 (2118 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Associated Targets(non-human)

Agtr2 Angiotensin II type 2 (AT-2) receptor (803 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Mc4r Melanocortin receptor 4 (1205 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Ltc4s Leukotriene C4 synthase (1 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Sigmar1 Sigma opioid receptor (160 Activities)

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Npy1r Neuropeptide Y receptor type 1 (8 Activities)

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Cruzipain (33337 Activities)

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Cckar Cholecystokinin A receptor (90 Activities)

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Abcb1b P-glycoprotein 1 (174 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Nos2 Nitric oxide synthase, inducible (3573 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Mapk1 MAP kinase ERK2 (650 Activities)

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Mmp9 Matrix metalloproteinase 9 (38 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Pseudomonas aeruginosa (123386 Activities)

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Klebsiella pneumoniae (43867 Activities)

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Staphylococcus aureus (210822 Activities)

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Acinetobacter baumannii (41033 Activities)

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Escherichia coli (133304 Activities)

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Pneumocystis carinii (749 Activities)

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Leishmania infantum (5912 Activities)

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Trypanosoma brucei (78846 Activities)

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Trypanosoma brucei brucei (13300 Activities)

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Entamoeba histolytica (2676 Activities)

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Cryptosporidium parvum (1150 Activities)

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Plasmodium falciparum (966862 Activities)

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Cryptococcus neoformans (21258 Activities)

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Candida albicans (78123 Activities)

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Leishmania amazonensis (3813 Activities)

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Leishmania donovani (89745 Activities)

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Leishmania major (2877 Activities)

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Leishmania mexicana (936 Activities)

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Trypanosoma cruzi (99888 Activities)

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Trichomonas vaginalis (2376 Activities)

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Toxoplasma gondii (4585 Activities)

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Rattus norvegicus (775804 Activities)

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Trypanosoma brucei rhodesiense (7991 Activities)

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Npsr1 Neuropeptide S receptor (260 Activities)

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rep Replicase polyprotein 1ab (378 Activities)

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Nfe2l2 Nuclear factor erythroid 2-related factor 2 (214 Activities)

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bioA Adenosylmethionine-8-amino-7-oxononanoate aminotransferase (298 Activities)

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Glra2 Glycine receptor (1745 Activities)

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Mechanisms of Action

Chemical and Physical Properties

• Solubility: Solvent:DMSO, Max Conc. mg/mL: 19.23, Max Conc. mM: 50; Solvent:ethanol, Max Conc. mg/mL: 7.69, Max Conc. mM: 20
• Specific Rotation[α]: 11° (C=2,CHCl3)
• Melt Point(°C): 218 °C
• Molecular Weight: 384.500 g/mol
• XLogP3: 3.100
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 384.23 Da
• Monoisotopic Mass: 384.23 Da
• Topological Polar Surface Area: 60.400 Ų
• Heavy Atom Count: 28
• Formal Charge: 0
• Complexity: 820.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 6
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

References

1. Zu Qiang Jiang, Lei Zhang, Cui Juan Lan, Jian Ping Wang.  (2023)  Development of a Progesterone-Receptor-Based Pseudo-immunoassay for Multi-detection of Progestins in Milk and Studying Its Recognition Mechanism.  JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY,      [PMID:37938156] [10.1021/acs.jafc.3c05890]

2. Yan Su, Gelin Liu, Haozhe Hou, Yaojia Peng, Jianping Wang.  (2023)  Development of a Magnetic Molecularly Imprinted Microsphere-Based Signal Amplified Semi-Homogeneous Method for Multidetection of Five Progestins in Milk.  Foods,  12  (15): (2818).  [PMID:37569089] [10.3390/foods12152818]

3. Mai Luo, Yifan Hua, Yiran Liang, Jiajun Han, Donghui Liu, Wenting Zhao, Peng Wang.  (2017)  Synthesis of novel β-cyclodextrin functionalized S, N codoped carbon dots for selective detection of testosterone.  BIOSENSORS & BIOELECTRONICS,      [PMID:28683411] [10.1016/j.bios.2017.06.056]

4. Aining Yin, Yu Fu, Tingxin Wang, Honglin Li, Xiufang Wang, Xueke Ye, Peipei Dong, Wei Yao.  (2024)  Fu-Zheng-Li-Fei Recipe (FZLFR) in the treatment of cancer cachexia: Exploration of the efficacy and molecular mechanism based on chemical characterization, experimental research and network pharmacology.  JOURNAL OF ETHNOPHARMACOLOGY,      [PMID:39395766] [10.1016/j.jep.2024.118929]