Spironolactone: Difference between revisions

Spironolactone
	File:Spironolactone.png
Clinical data
Pregnancy; category	C (USA); B3 (Aus);
ATC code	C03DA01 (WHO) ;
Legal status
Legal status	US: WARNING;
Pharmacokinetic data
Elimination half-life	10 minutes
Identifiers
CAS Number	52-01-7;
PubChem CID	5833;
DrugBank	APRD01234;
CompTox Dashboard (EPA)	DTXSID6034186 ;
ECHA InfoCard	100.000.122
Chemical and physical data
Formula	C24H32O4S
Molar mass	416.574 g/mol

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Revision as of 15:48, 21 June 2006

Spironolactone (marketed as Aldactone®, Novo-Spiroton®, Spiractin®, Spirotone®, or Berlactone®) is a synthetic 17-lactone steroid which is a renal competitive aldosterone antagonist in a class of pharmaceuticals called potassium-sparing diuretics, used primarily to treat low-renin hypertension, hypokalemia, and Conn's syndrome. On its own, spironolactone is only a weak diuretic, but it can be combined with other diuretics. Due to its anti-androgen effect, it can also be used to treat hirsutism, and is a common component in hormone therapy for male-to-female transgendered people. Also used for treating hair loss.

Mechanism of action

Spironolactone inhibits the effect of aldosterone by competing for intracellular aldosterone receptor in the distal tubule cells. This increases the secretion of water and sodium, while decreasing the excretion of potassium. Spironolactone has a fairly slow onset of action, taking several days to develop and similarly the effect diminishes slowly. Spironolactone has anti-androgen activity by binding to the androgen receptor and thus preventing it to interact with dihydrotestosterone.^[2]

Pharmacokinetics

Spironolactone is fairly rapidly absorbed from the gastrointestinal tract. It is also rapidly metabolised and bound in plasma proteins. Many of its metabolites are also active and one of them, canrenone as potassium canrenoate, is used parenterally when rapid effect is needed. Spironolactone's half-life is only 10 minutes, but canrenone's half-life is 10 to 35 hours, depending on the dose. The main elimination route is in the urine and some also in the bile.

Adverse effects

Spironolactone can cause gastrointestinal problems fairly often. Since it also affects steroid receptors elsewhere in the body, it can cause gynecomastia, menstrual irregularities and testicular atrophy. Other side effects include ataxia, impotence, drowsiness and rashes. A carcinogenic effect has been demonstrated in rats. [2]

References

^ "FDA-sourced list of all drugs with black box warnings (Use Download Full Results and View Query links.)". nctr-crs.fda.gov. FDA. Retrieved 22 Oct 2023.
^ Antiandrogen effect [1]

External links

nih.gov information site

[FDA-AllBoxedWarnings-1] "FDA-sourced list of all drugs with black box warnings (Use Download Full Results and View Query links.)". nctr-crs.fda.gov. FDA. Retrieved 22 Oct 2023.

[2] Antiandrogen effect [1]

[1]

[2]

@@ Line 1: / Line 1: @@
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+| IUPAC_name =
-|-
+| image = {{PAGENAME}}.png
-| bgcolor="#ffffff" align="center" colspan="2" |
+| CAS_number = 52-01-7
-[[Image:Spironolactone.png|200px|Spironolactone chemical structure]]<br/>
+| ATC_prefix = C03
-''Spironolactone''
+| ATC_suffix = DA01
-|-
+| ATC_supplemental =
-| align="center" colspan="2" | ''7&alpha;-Acetylthio-3-oxo-17&alpha;-pregn-4-ene-21,17&beta;-carbolactone acid-&gamma;-lactone''
+| PubChem = 5833
-|- align="center" style="border-bottom: 3px solid gray"
+| DrugBank = APRD01234
-| '''[[CAS number]]''' <br/> 52-01-7
+| chemical_formula = C<sub>24</sub>H<sub>32</sub>O<sub>4</sub>S
-| '''[[ATC code]]'''   <br/> C03DA01
+| molecular_weight = 416.574 g/mol
-|-
+| bioavailability =
-| bgcolor="#eeeeee" | [[Chemical formula]]
+| protein_bound =
-| bgcolor="#ddeeff" | C<sub>24</sub>H<sub>32</sub>O<sub>4</sub>S
+| metabolism =
-|-
+| elimination_half-life = 10 minutes
-| bgcolor="#eeeeee" | [[Molecular weight]]
+| pregnancy_category = C (USA); B3 (Aus)
-| bgcolor="#ddeeff" | 416.57
+| legal_status =
-|-
+| routes_of_administration =
-| bgcolor="#eeeeee" | [[Bioavailability]]
+}}
-| bgcolor="#ddeeff" | ?
-|-
-| bgcolor="#eeeeee" | Metabolism
-| bgcolor="#ddeeff" | ?
-|-
-| bgcolor="#eeeeee" | [[Elimination half-life]]
-| bgcolor="#ddeeff" | ?
-|-
-| bgcolor="#eeeeee" | [[Excretion]]
-| bgcolor="#ddeeff" | ?
-|-
-| bgcolor="#eeeeee" | [[Pregnancy category (pharmaceutical)|Pregnancy category]]
-| bgcolor="#ddeeff" | C ([[United States|USA]]) <br /> B3 ([[Australia|Aus]])
-|-
-| bgcolor="#eeeeee" | [[Regulation of therapeutic goods|Legal status]]
-| bgcolor="#ddeeff" | ?
-|-
-| bgcolor="#eeeeee" | Routes of administration
-| bgcolor="#ddeeff" | ?
-|-
-|}
 '''Spironolactone''' (marketed as '''Aldactone'''&reg;, '''Novo-Spiroton'''&reg;, '''Spiractin'''&reg;, '''Spirotone'''&reg;, or '''Berlactone'''&reg;) is a synthetic 17-[[lactone]] [[steroid]] which is a renal competitive [[aldosterone]] antagonist in a class of [[pharmaceutical]]s called [[potassium]]-sparing [[diuretic]]s, used primarily to treat low-[[renin]] [[hypertension]], [[hypokalemia]], and [[Conn's syndrome]].  On its own, spironolactone is only a weak diuretic,  but it can be combined with other diuretics. Due to its anti-[[androgen]] effect, it can also be used to treat [[hirsutism]], and is a common component in [[Hormone replacement therapy (trans)|hormone therapy]] for male-to-female [[transgender]]ed people. Also used for treating hair loss.