Zuranolone information

Zuranolone
Clinical data
Pronunciation	/zʊˈrænəloʊn/; zuu-RAN-ə-lohn
Trade names	Zurzuvae
Other names	SAGE-217; S-812217; SGE-797; BIIB-125
License data	US DailyMed: Zuranolone;
Pregnancy; category	Contraindicated;
Routes of; administration	By mouth
Drug class	Neurosteroid; GABAA receptor positive allosteric modulator
ATC code	None;
Legal status
Legal status	US: Schedule IV;
Pharmacokinetic data
Protein binding	99.5%[unreliable medical source?]
Metabolism	CYP3A4[unreliable medical source?]
Elimination half-life	16–23 hours
Identifiers
	IUPAC name 1-(2-((3R,5R,8R,9R,10S,13S,14S,17S)-3-Hydroxy-3,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)-2-oxoethyl)-1H-pyrazole-4-carbonitrile;
CAS Number	1632051-40-1;
PubChem CID	86294073;
DrugBank	DB15490;
ChemSpider	71117610;
UNII	7ZW49N180B;
KEGG	D11793;
ChEBI	CHEBI:228302;
ChEMBL	ChEMBL4105630;
ECHA InfoCard	100.271.331
Chemical and physical data
Formula	C25H35N3O2
Molar mass	409.574 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O=C(CN1N=CC(C#N)=C1)[C@H]2CC[C@@]3([H])[C@]4([H])CC[C@]5([H])C[C@](C)(O)CC[C@]5([H])[C@@]4([H])CC[C@@]32C;
	InChI InChI=1S/C25H35N3O2/c1-24(30)9-7-18-17(11-24)3-4-20-19(18)8-10-25(2)21(20)5-6-22(25)23(29)15-28-14-16(12-26)13-27-28/h13-14,17-22,30H,3-11,15H2,1-2H3/t17-,18+,19-,20-,21+,22-,24-,25+/m1/s1; Key:HARRKNSQXBRBGZ-GVKWWOCJSA-N;

Zuranolone, sold under the brand name Zurzuvae, is a medication used for the treatment of postpartum depression.^[5]^[6] It is taken by mouth.^[5]

The most common side effects include drowsiness, dizziness, diarrhea, fatigue, nasopharyngitis, and urinary tract infection.^[5]^[6] An orally active inhibitory pregnane neurosteroid, zuranolone acts as a positive allosteric modulator of the GABA_A receptor.^[7]^[8]^[9]

Zuranolone was approved for medical use in the United States for the treatment of postpartum depression in August 2023.^[6] It was developed by Sage Therapeutics and Biogen.^[10]

^ "Schedules of Controlled Substances: Placement of Zuranolone in Schedule IV". Federal Register. 31 October 2023. Retrieved 5 March 2024.
^ ^a ^b "Zuranolone". DrugBank Online.
^ Cerne R, Lippa A, Poe MM, Smith JL, Jin X, Ping X, et al. (2022). "GABAkines - Advances in the discovery, development, and commercialization of positive allosteric modulators of GABA_A receptors". Pharmacology & Therapeutics. 234: 108035. doi:10.1016/j.pharmthera.2021.108035. PMC 9787737. PMID 34793859. S2CID 244280839.
^ Faden J, Citrome L (2020). "Intravenous brexanolone for postpartum depression: what it is, how well does it work, and will it be used?". Therapeutic Advances in Psychopharmacology. 10: 2045125320968658. doi:10.1177/2045125320968658. PMC 7656877. PMID 33224470.
^ ^a ^b ^c "Zurzuvae (zuranolone) capsules, for oral use, [controlled substance schedule pending]" (PDF). Archived (PDF) from the original on 5 August 2023. Retrieved 5 August 2023.
^ ^a ^b ^c Cite error: The named reference FDA PR 20230804 was invoked but never defined (see the help page).
^ "SAGE 217". AdisInsight. Archived from the original on 29 March 2019. Retrieved 10 February 2018.
^ Blanco MJ, La D, Coughlin Q, Newman CA, Griffin AM, Harrison BL, et al. (2018). "Breakthroughs in neuroactive steroid drug discovery". Bioorganic & Medicinal Chemistry Letters. 28 (2): 61–70. doi:10.1016/j.bmcl.2017.11.043. PMID 29223589.
^ Martinez Botella G, Salituro FG, Harrison BL, Beresis RT, Bai Z, Blanco MJ, et al. (2017). "Neuroactive Steroids. 2. 3α-Hydroxy-3β-methyl-21-(4-cyano-1H-pyrazol-1'-yl)-19-nor-5β-pregnan-20-one (SAGE-217): A Clinical Next Generation Neuroactive Steroid Positive Allosteric Modulator of the (γ-Aminobutyric Acid)_A Receptor". Journal of Medicinal Chemistry. 60 (18): 7810–7819. doi:10.1021/acs.jmedchem.7b00846. PMID 28753313.
^ Saltzman J (4 August 2023). "FDA approves postpartum depression pill from two Cambridge drug firms". The Boston Globe. Archived from the original on 6 August 2023. Retrieved 5 August 2023.

[Federal_Register_2023_f960-1] "Schedules of Controlled Substances: Placement of Zuranolone in Schedule IV". Federal Register. 31 October 2023. Retrieved 5 March 2024.

[auto-2] "Zuranolone". DrugBank Online.

[Cerne2022-3] Cerne R, Lippa A, Poe MM, Smith JL, Jin X, Ping X, et al. (2022). "GABAkines - Advances in the discovery, development, and commercialization of positive allosteric modulators of GABA_A receptors". Pharmacology & Therapeutics. 234: 108035. doi:10.1016/j.pharmthera.2021.108035. PMC 9787737. PMID 34793859. S2CID 244280839.

[Faden2020-4] Faden J, Citrome L (2020). "Intravenous brexanolone for postpartum depression: what it is, how well does it work, and will it be used?". Therapeutic Advances in Psychopharmacology. 10: 2045125320968658. doi:10.1177/2045125320968658. PMC 7656877. PMID 33224470.

[Zurzuvae_FDA_label-5] "Zurzuvae (zuranolone) capsules, for oral use, [controlled substance schedule pending]" (PDF). Archived (PDF) from the original on 5 August 2023. Retrieved 5 August 2023.

[FDA_PR_20230804-6] Cite error: The named reference FDA PR 20230804 was invoked but never defined (see the help page).

[AdisInsight-7] "SAGE 217". AdisInsight. Archived from the original on 29 March 2019. Retrieved 10 February 2018.

[Blanco2018-8] Blanco MJ, La D, Coughlin Q, Newman CA, Griffin AM, Harrison BL, et al. (2018). "Breakthroughs in neuroactive steroid drug discovery". Bioorganic & Medicinal Chemistry Letters. 28 (2): 61–70. doi:10.1016/j.bmcl.2017.11.043. PMID 29223589.

[Botella2017-9] Martinez Botella G, Salituro FG, Harrison BL, Beresis RT, Bai Z, Blanco MJ, et al. (2017). "Neuroactive Steroids. 2. 3α-Hydroxy-3β-methyl-21-(4-cyano-1H-pyrazol-1'-yl)-19-nor-5β-pregnan-20-one (SAGE-217): A Clinical Next Generation Neuroactive Steroid Positive Allosteric Modulator of the (γ-Aminobutyric Acid)_A Receptor". Journal of Medicinal Chemistry. 60 (18): 7810–7819. doi:10.1021/acs.jmedchem.7b00846. PMID 28753313.

[10] Saltzman J (4 August 2023). "FDA approves postpartum depression pill from two Cambridge drug firms". The Boston Globe. Archived from the original on 6 August 2023. Retrieved 5 August 2023.

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Clinical data

Pronunciation	/zʊˈrænəloʊn/ zuu-RAN-ə-lohn
Trade names	Zurzuvae
Other names	SAGE-217; S-812217; SGE-797; BIIB-125
License data	US DailyMed: Zuranolone
Pregnancy category	Contraindicated
Routes of administration	By mouth
Drug class	Neurosteroid; GABA_A receptor positive allosteric modulator
ATC code	None
Legal status
Legal status	US: Schedule IV^[1]
Pharmacokinetic data
Protein binding	99.5%^[2]^{[unreliable medical source?]}
Metabolism	CYP3A4^[2]^{[unreliable medical source?]}
Elimination half-life	16–23 hours^[3]^[4]
Identifiers
IUPAC name 1-(2-((3R,5R,8R,9R,10S,13S,14S,17S)-3-Hydroxy-3,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)-2-oxoethyl)-1H-pyrazole-4-carbonitrile
CAS Number	1632051-40-1
PubChem CID	86294073
DrugBank	DB15490
ChemSpider	71117610
UNII	7ZW49N180B
KEGG	D11793
ChEBI	CHEBI:228302
ChEMBL	ChEMBL4105630
ECHA InfoCard	100.271.331
Chemical and physical data
Formula	C₂₅H₃₅N₃O₂
Molar mass	409.574 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES O=C(CN1N=CC(C#N)=C1)[C@H]2CC[C@@]3([H])[C@]4([H])CC[C@]5([H])C[C@](C)(O)CC[C@]5([H])[C@@]4([H])CC[C@@]32C
InChI InChI=1S/C25H35N3O2/c1-24(30)9-7-18-17(11-24)3-4-20-19(18)8-10-25(2)21(20)5-6-22(25)23(29)15-28-14-16(12-26)13-27-28/h13-14,17-22,30H,3-11,15H2,1-2H3/t17-,18+,19-,20-,21+,22-,24-,25+/m1/s1 Key:HARRKNSQXBRBGZ-GVKWWOCJSA-N