Spironolactone

A summary of the most common chemical descriptors (InChI Key and SMILES codes) for Spironolactone are summarized together with 3D and 2D structures and relevant physico-chemical properties.

What is the Spironolactone?

The molecule Spironolactone presents a molecular formula of C13H11N3O4S2 and its IUPAC name is S-[(7R,8R,9S,10R,13S,14S,17R)-10,13-dimethyl-3,5'-dioxospiro[2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthrene-17,2'-oxolane]-7-yl] ethanethioate.

Spironolactone is a synthetic steroid molecule that is used as a diuretic and antihypertensive drug. It is a white, crystalline powder that is insoluble in water. Spironolactone is structurally similar to the hormone aldosterone and acts as a competitive antagonist at the aldosterone receptor. This results in a decrease in the reabsorption of salt and water by the kidneys and a decrease in blood volume and blood pressure. Spironolactone is used to treat hypertension, edema, and heart failure. It is also used as a treatment for acne and hirsutism in women..

3D structure

Cartesian coordinates

Geometry of Spironolactone in x, y and z coordinates (Å units) to copy/paste elsewhere. Generated with Open Babel software.

2D drawing

 

Spironolactone LZNWYQJJBLGYLT-UHFFFAOYSA-N chemical compound 2D structure molecule svg
Spironolactone

 

Molecule descriptors

 
IUPAC nameS-[(7R,8R,9S,10R,13S,14S,17R)-10,13-dimethyl-3,5'-dioxospiro[2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthrene-17,2'-oxolane]-7-yl] ethanethioate
InChI codeInChI=1S/C13H11N3O4S2/c1-16-10(13(18)15-9-4-2-3-6-14-9)11(17)12-8(5-7-21-12)22(16,19)20/h2-7,17H,1H3,(H,14,15,18)
InChI KeyLZNWYQJJBLGYLT-UHFFFAOYSA-N
SMILESCN1C(C(=O)Nc2ccccn2)=C(O)c2sccc2S1(=O)=O

Other names (synonyms)

IUPAC nomenclature provides a standardized method for naming chemical compounds. Although this system is widely used in chemistry, many chemical compounds have also other names commonly used in different contexts. These synonyms can come from a variety of sources and are used for a variety of purposes.

One common source of synonyms for chemical compounds is the common or trivial names, assigned on the basis of appearance, properties, or origin of the molecule.

Another source of synonyms are historical or obsolete names employed in the past, however replaced nowadays by more modern or standardized names.

In addition to common and historical names, chemical compounds may also have synonyms that are specific to a particular field or industry.

  • (7?,17?)-7-(Acetylthio)-17-hydroxy-3-oxopregn-4-ene-21-carboxylic acid ?-lactone
  • 082S250
  • 17-HYDROXY-7.ALPHA.-MERCAPTO-3-OXO-17.ALPHA.-PREGN-4-ENE-21-CARBOXYLIC ACID, .GAMMA.-LACTONE ACETATE
  • 17-HYDROXY-7ALPHA-MERCAPTO-3-OXO-17ALPHA-PREGN-4-ENE-21- CARBOXYLIC ACID; GAMMA-LACTONE ACETATE
  • 17-Hydroxy-7-alpha-mercapto-3-oxo-17-alpha-pregn-4-ene-21-carboxylic acid-gamma-lactone-7-acetate
  • 17-Hydroxy-7alpha-mercapto-3-oxo-17alpha-pregn-4-ene-21-carboxylic acid, gamma-lactone acetate
  • 17-alpha-Pregn-4-ene-21-carboxylic acid, 17-hydroxy-7-alpha-mercapto-3-oxo-, gamma-lactone acetate
  • 17.alpha.-Pregn-4-ene-21-carboxylic acid, .gamma.-lactone acetate
  • 17.alpha.-Pregn-4-ene-21-carboxylic acid, .gamma.-lactone, acetate
  • 17alpha-Pregn-4-ene-21-carboxylic acid, 17-hydroxy-7alpha-mercapto-3-oxo-, gamma-lactone, acetate
  • 27O7W4T232
  • 2oax
  • 3'-(3-Oxo-7-alpha-acetylthio-17-beta-hydroxyandrost-4-en-17-beta-yl)propionic acid lactone
  • 3-(3-Keto-7-alpha-acetylthio-17-beta-hydroxy-4-androsten-17-alpha-yl)propionic acid lactone
  • 3-(3-Keto-7.alpha.-acetylthio-17.beta.-hydroxy-4-androsten-17.alpha.-yl)propionic acid lactone
  • 3vhu
  • 52-01-7
  • 7-.alpha.-(acetylthio)-17-.alpha.-hydroxy-3-oxopregn-4-ene-21-carboxylic acid, .gamma.-lactone
  • 7-alpha-(acetylthio)-17-alpha-hydroxy-3-oxopregn-4-ene-21-carboxylic acid, gamma-lactone
  • 7-alpha-Acetylthio-3-oxo-17-alpha-pregn-4-ene-21,17-beta-carbolactone
  • 7alpha-(acetylsulfanyl)-3-oxo-17alpha-pregn-4-ene-21,17-carbolactone
  • AB00513806
  • AB01275520-01
  • AB01275520_02
  • AC-4214
  • ACT02596
  • ALDACTAZIDE COMPONENT SPIRONOLACTONE
  • AMY40521
  • Abbolactone
  • Acelat
  • Aldace
  • Aldactide
  • Aldactone
  • Aldactone A
  • Alderon
  • Aldopur
  • Almatol
  • Altex
  • Aquareduct
  • BDBM50228080
  • BIDD:PXR0071
  • BPBio1_000194
  • BRN 0057767
  • BS166385
  • BSPBio_000176
  • Berlactone
  • C07310
  • C75438
  • CARDALIS COMPONENT SPIRONOLACTONE
  • CCG-220128
  • CPD000471892
  • Carospir
  • D00443
  • DB00421
  • DSSTox_CID_14186
  • DSSTox_GSID_34186
  • DSSTox_RID_79120
  • Deverol
  • Diatense
  • Dira
  • Espironolactona
  • Euteberol
  • GTPL2875
  • HMS1568I18
  • HMS2090N21
  • HMS2095I18
  • HMS2236E06
  • HMS3259G11
  • HMS3712I18
  • HSDB 3184
  • HY-B0561
  • KS-5234
  • MFCD00082250
  • MLS001074672
  • MLS001333253
  • MLS001333254
  • MLS002153245
  • MLS002207058
  • MLS002548846
  • Melarcon
  • NC00482
  • NCGC00015948-02
  • NCGC00164397-01
  • NCGC00164397-02
  • NCGC00164397-03
  • NCGC00164397-05
  • NCGC00255229-01
  • NSC 150399
  • NSC-150399
  • NSC150399
  • PREGN-4-ENE-21-CARBOXYLIC ACID, 7-(ACETYLTHIO)-17-HYDROXY-3-OXO-,.GAMMA.-LACTONE, (7.ALPHA.,17.ALPHA.)-
  • Pregn-4-ene-21-carboxylic acid, .gamma.-lactone, (7.alpha.,17.alpha.)-
  • Pregn-4-ene-21-carboxylic acid, 7-(acetylthio)-17-hydroxy-3-oxo-, gamma-lactone, (7alpha,17alpha)-
  • Prestwick0_000128
  • Prestwick1_000128
  • Prestwick2_000128
  • Prestwick3_000128
  • Q-201737
  • Q422188
  • S-[(7R,8R,9S,10R,13S,14S,17R)-10,13-dimethyl-3,5'-dioxospiro[2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthrene-17,2'-oxolane]-7-yl] ethanethioate
  • S0260
  • SC 15983
  • SC 9420
  • SC-9420
  • SC9420
  • SMR000471892
  • SPIRONOLACTONE COMPONENT CARDALIS
  • SPIRONOLACTONE COMPONENT OF ALDACTAZIDE
  • SR-01000765419
  • SR-01000765419-2
  • SR-05000000452
  • SR-05000000452-2
  • Spiranolactone
  • Spiresis
  • Spiridon
  • Spiro(17H-cyclopenta(a)phenauthrene-17,2'-(3'H)-furan)
  • Spiro-Tablinen
  • Spiro[17H-cyclopenta[a]phenauthrene-17,2'-(3'H)-furan]
  • Spiroctan
  • Spirolactone
  • Spirolang
  • Spirone
  • Spironocompren
  • Spironolactone
  • Spironolactone (JP17/USP/INN)
  • Spironolactone 1.0 mg/ml in Acetonitrile
  • Spironolactone A
  • Spironolactone ceva
  • Spironolactonum
  • Uractone
  • Urusonin
  • Verospiron
  • Verospirone
  • WLN: L E5 B666 FX OV MUTJ A1 E1 KSV1 F-& CT5VOXTJ
  • Xenalon
  • Z1551900341
  • s4054
  • spironolactone
  • spironolattone
  • spirotone

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC3861599
  • CAS-52-01-7
  • UNII-27O7W4T232
  • AKOS015896401
  • BRD-K90027355-001-03-4
  • BRD-K90027355-001-19-0
  • DTXSID6034186
  • CHEMBL1393
  • CHEBI:9241
  • Tox21_113047
  • Tox21_302154
  • EINECS 200-133-6
  • SPBio_002115
  • SCHEMBL20939

Physico-Chemical properties

IUPAC nameS-[(7R,8R,9S,10R,13S,14S,17R)-10,13-dimethyl-3,5'-dioxospiro[2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthrene-17,2'-oxolane]-7-yl] ethanethioate
Molecular formulaC13H11N3O4S2
Molecular weight337.374
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity85.40
LogP2.7
Topological polar surface area136.2

LogP and topological polar surface area (TPSA) values were estimated using Open Babel software.

The n-octanol/water partition coeficient (Kow) data is applied in toxicology and drug research. Kow values are used, to guess the environmental fate of persistent organic pollutants. High partition coefficients values, tend to accumulate in the fatty tissue of organisms. Molecules with a log(Kow) (or LogP) greater than 5 are considered to bioaccumulate.

TPSA values are the sum of the surface area over all polar atoms or molecules, mainly oxygen and nitrogen, also including hydrogen atoms.

In medicinal chemistry, TPSA is used to assess the ability of a drug to permeabilise cells.

For molecules to penetrate the blood-brain barrier (and act on receptors in the central nervous system), TPSA values below 90 Å2 are required. Thus, molecules with a polar surface area greater than 140 Å2 tend to be poorly permeable to cell membranes.