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Aurothioglucose
Clinical data
Synonyms	Gold thioglucose, Solganal, Auromyose
AHFS/Drugs.com	Consumer Drug Information
Routes of; administration	Intramuscular injection
ATC code	M01CB04 (WHO) ;
Pharmacokinetic data
Bioavailability	0%
Identifiers
	IUPAC name gold(I) (2S,3S,4R,5S)-3,4,5-trihydroxy-; 6-(hydroxymethyl)-oxane-2-thiolate;
CAS Number	12192-57-3 ;
PubChem CID	6104;
ChemSpider	16738764 ;
UNII	2P2V9Q0E78;
ChEMBL	ChEMBL1697725 ;
E number	{{#property:P628}}
ECHA InfoCard	{{#property:P2566}}Lua error in Module:EditAtWikidata at line 36: attempt to index field 'wikibase' (a nil value).
Chemical and physical data
Formula	C6H11AuO5S
Molar mass	392.181 g/mol
3D model (JSmol)	Interactive image;
	SMILES O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1S[Au];
	InChI InChI=1S/C6H12O5S.Au/c7-1-2-3(8)4(9)5(10)6(12)11-2;/h2-10,12H,1H2;/q;+1/p-1/t2-,3-,4+,5-,6-;/m1./s1 ; Key:XHVAWZZCDCWGBK-WYRLRVFGSA-M ;
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VisualWikitext

Latest revision as of 13:06, 13 April 2015

Editor-In-Chief: C. Michael Gibson, M.S., M.D. [1]

Overview

Aurothioglucose, also known as gold thioglucose, is a chemical compound with the formula AuSC₆H₁₁O₅. This derivative of the sugar glucose was formerly used to treat rheumatoid arthritis.

History

Throughout history, gold was used to cure diseases, although the efficacy was not established. In 1935, gold drugs were reported to be effective for the treatment of rheumatoid arthritis.^[1] Although many patients reacted positively to the drug, gold thioglucose was not uniformly effective.

Three gold drugs remain in active clinical use for this purpose in the United States: auranofin, sodium aurothiomalate (gold sodium thiomalate) and aurothioglucose. In the United Kingdom, only sodium aurothiomalate and auranofin are used.

In 2001, aurothoglucose was withdrawn from the Dutch marked, where it had been the only injectable gold preparation available since 1943, forcing hospitals to change medication for a large number of patients to aurothiomalate.^[2] The drug had been in use for more than 70 years, and four years later the reasons for its sudden disappearance remained unclear.^[3]

Medicinal chemistry

Gold thioglucose features gold in the oxidation state of +I, like other gold thiolates. It is a water-soluble, non-ionic species that is assumed to exist as a polymer.^[1] Under physiological conditions, an oxidation-reduction reaction leads to the formation of metallic gold and sulfinic acid derivative of thioglucose.

2 AuSTg → 2 Au + TgSSTg

TgSSTg + H₂O → TgSOH + TgSH

2 TgSOH → TgSO₂H + TgSH

Overall: 2 H₂O + 4 AuSTg → 4 Au + TgSO₂H + 3 TgSH

(where AuSTg = gold thioglucose, TgSSTg = thioglucose disulfide, TgSO₂H = sulfinic acid derivative of thioglucose)

Preparation

Gold thioglucose can be prepared by treating gold bromide with thioglucose solution saturated with sulfur dioxide. Gold thioglucose is precipitated with methanol and recrystallized with water and methanol.

Miscellaneous observations

In recent research, it was found that injection of gold thioglucose in the mouse induces obesity.^[4] Aurothioglucose has an interaction with the antimalarial medication hydroxychloroquine.

References

↑ ^1.0 ^1.1 Shaw, III, C. F. (1999). "Gold-Based Therapeutic Agents". Chemical Reviews. 99 (9): 2589–600. doi:10.1021/cr980431o. PMID 11749494.
↑ Parenteral gold preparations. Efficacy and safety of therapy after switching from aurothioglucose to aurothiomalate (van Roon et al, J Rheumatol 2005)
↑ PMID 15940754 (PMID 15940754)
Citation will be completed automatically in a few minutes. Jump the queue or expand by hand
↑ Naruta E, Buko V (2001). "Hypolipidemic effect of pantothenic acid derivatives in mice with hypothalamic obesity induced by aurothioglucose". Exp Toxicol Pathol. 53 (5): 393–8. doi:10.1078/0940-2993-00205. PMID 11817109.

[shaw-1] 1.0 ^1.1 Shaw, III, C. F. (1999). "Gold-Based Therapeutic Agents". Chemical Reviews. 99 (9): 2589–600. doi:10.1021/cr980431o. PMID 11749494.

[2] Parenteral gold preparations. Efficacy and safety of therapy after switching from aurothioglucose to aurothiomalate (van Roon et al, J Rheumatol 2005)

[3] PMID 15940754 (PMID 15940754)
Citation will be completed automatically in a few minutes. Jump the queue or expand by hand

[4] Naruta E, Buko V (2001). "Hypolipidemic effect of pantothenic acid derivatives in mice with hypothalamic obesity induced by aurothioglucose". Exp Toxicol Pathol. 53 (5): 393–8. doi:10.1078/0940-2993-00205. PMID 11817109.

[1]

[2]

[3]

[4]

@@ Line 1: / Line 1: @@
-{{drugbox |
+{{Drugbox
+| Verifiedfields = changed
+| verifiedrevid = 447574504
 | IUPAC_name = gold(I) (2''S'',3''S'',4''R'',5''S'')-3,4,5-trihydroxy-<br>6-(hydroxymethyl)-oxane-2-thiolate
 | image = Authioglucose.png
@@ Line 5: / Line 7: @@
 | image2 = Aurothioglucose-3D-vdW.png
 | width2 = 250
+<!--Clinical data-->
+| tradename =
+| Drugs.com = {{drugs.com|CDI|aurothioglucose}}
+| MedlinePlus =
+| licence_EU = <!-- EMEA requires brand name -->
+| licence_US = <!-- FDA may use generic name -->
+| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
+| pregnancy_US = <!-- A / B            / C / D / X -->
+| pregnancy_category =
+| legal_AU = <!-- Unscheduled / S2 / S3 / S4  / S8 -->
+| legal_CA = <!--                             / Schedule I, II, III, IV, V, VI, VII, VIII -->
+| legal_UK = <!-- Not form found in UK - rather Sodium Aurothiomalate & Auranofin -->
+| legal_US = <!-- OTC                   / Rx-only  / Schedule I, II, III, IV, V -->
+| legal_status =
+| dependency_liability =
+| routes_of_administration = [[Intramuscular injection]]
+<!--Pharmacokinetic data-->
+| bioavailability = 0%
+| protein_bound =
+| metabolism =
+| elimination_half-life =
+| excretion =
+<!--Identifiers-->
+| CAS_number_Ref = {{cascite|correct|??}}
 | CAS_number = 12192-57-3
-| CAS_supplemental =
+| ATC_prefix = M01
-| ATC_prefix=M01
+| ATC_suffix = CB04
-| ATC_suffix=CB04
+| ATC_supplemental =
-| ATC_supplemental=
 | PubChem = 6104
-| DrugBank =
+| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
-| C=6 | H=11 | Au=1 | O=5 | S=1
+| DrugBank =
+| ChEMBL_Ref = {{ebicite|changed|EBI}}
+| ChEMBL = 1697725
+| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
+| ChemSpiderID = 16738764
+| UNII_Ref = {{fdacite|correct|FDA}}
+| UNII = 2P2V9Q0E78
+<!--Chemical data-->
+| C=6 | H=11 | Au=1 | O=5 | S=1
 | molecular_weight = 392.181 g/mol
+| smiles = O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1S[Au]
+| InChI = 1/C6H12O5S.Au/c7-1-2-3(8)4(9)5(10)6(12)11-2;/h2-10,12H,1H2;/q;+1/p-1/t2-,3-,4+,5-,6-;/m1./s1/rC6H11AuO5S/c7-13-6-5(11)4(10)3(9)2(1-8)12-6/h2-6,8-11H,1H2/t2-,3-,4+,5-,6-/m1/s1
+| InChIKey = XHVAWZZCDCWGBK-MOEPNNSPBJ
+| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
+| StdInChI = 1S/C6H12O5S.Au/c7-1-2-3(8)4(9)5(10)6(12)11-2;/h2-10,12H,1H2;/q;+1/p-1/t2-,3-,4+,5-,6-;/m1./s1
+| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
+| StdInChIKey = XHVAWZZCDCWGBK-WYRLRVFGSA-M
 | synonyms = Gold thioglucose, Solganal, Auromyose
-| bioavailability = 0%
-| protein_bound =
-| metabolism =
-| elimination_half-life =
-| excretion =
-| licence_EU =    <!-- EMEA requires brand name -->
-| licence_US =    <!-- FDA may use generic name -->
-| pregnancy_AU =  <!-- A / B1 / B2 / B3 / C / D / X -->
-| pregnancy_US =  <!-- A / B            / C / D / X -->
-| pregnancy_category =
-| legal_AU =  <!-- Unscheduled / S2 / S3 / S4  / S8 -->
-| legal_CA =  <!--                             / Schedule I, II, III, IV, V, VI, VII, VIII -->
-| legal_UK =  <!-- Not form found in UK - rather Sodium Aurothiomalate & Auranofin -->
-| legal_US =  <!-- OTC                   / Rx-only  / Schedule I, II, III, IV, V -->
-| legal_status =
-| dependency_liability =
-| routes_of_administration = [[intramuscular]] injection
 }}
+              __NOTOC__
 {{SI}}
-{{EH}}
+{{CMG}}
 ==Overview==
-'''Aurothioglucose''', also known as gold thioglucose, is a [[chemical compound]] with the formula AuSC<sub>6</sub>H<sub>11</sub>O<sub>5</sub>. This derivative of the sugar [[glucose]] is used to treat [[rheumatoid arthritis]].
+'''Aurothioglucose''', also known as gold thioglucose, is a [[chemical compound]] with the formula AuSC<sub>6</sub>H<sub>11</sub>O<sub>5</sub>. This derivative of the sugar [[glucose]] was formerly used to treat [[rheumatoid arthritis]].
 ==History==
 {{main|Gold salts}}
-Throughout history, gold was used to cure diseases, although the efficacy was not established. In 1935, gold drugs were reported to be effective for the treatment rheumatoid arthritis.<ref name=shaw>{{cite journal | author=Shaw, III, C. F. | title=Gold-Based Therapeutic Agents| journal=Chemical Reviews | year=1999 | volume=99 | pages=2589-600 | doi=10.1021/cr980431o}}</ref> Although many patients reacted positively to the drug, gold thioglucose was not uniformly effective.
+Throughout history, gold was used to cure diseases, although the efficacy was not established. In 1935, gold drugs were reported to be effective for the treatment of [[rheumatoid arthritis]].<ref name=shaw>{{cite journal | author=Shaw, III, C. F. | title=Gold-Based Therapeutic Agents| journal=Chemical Reviews | year=1999 | volume=99 | pages=2589–600 | doi=10.1021/cr980431o | pmid=11749494 | issue=9}}</ref> Although many patients reacted positively to the drug, gold thioglucose was not uniformly effective.
-Two gold drugs remain in active clinical use for this purpose in the United States: [[sodium aurothiomalate]] (gold sodium thiomalate) and Aurothioglucose, sold under the trade names Myochrysine and Solgonal, respectively.  In the United Kingdom, only sodium aurothiomalate and [[auranofin]] are used.
+Three gold drugs remain in active clinical use for this purpose in the United States: [[auranofin]], [[sodium aurothiomalate]] (gold sodium thiomalate) and aurothioglucose.  In the United Kingdom, only sodium aurothiomalate and auranofin are used.
+In 2001, aurothoglucose was withdrawn from the Dutch marked, where it had been the only injectable gold preparation available since 1943, forcing hospitals to change medication for a large number of patients to aurothiomalate.<ref>''Parenteral gold preparations. Efficacy and safety of therapy after switching from aurothioglucose to aurothiomalate'' (van Roon et al, J Rheumatol 2005)</ref> The drug had been in use for more than 70 years, and four years later the reasons for its sudden disappearance remained unclear.<ref>{{cite pmid|15940754}}</ref>
 ==Medicinal chemistry==
@@ Line 49: / Line 80: @@
 Gold thioglucose features gold in the oxidation state of +I, like other gold thiolates. It is a water-soluble, non-ionic species that is assumed to exist as a polymer.<ref name=shaw/>  Under physiological conditions, an oxidation-reduction reaction leads to the formation of metallic gold and sulfinic acid derivative of thioglucose.
 :2 AuSTg  →  2 Au  +  TgSSTg
 :TgSSTg  +  H<sub>2</sub>O  →  TgSOH  +  TgSH
 :2 TgSOH  →  TgSO<sub>2</sub>H  +  TgSH
 :Overall: 2 H<sub>2</sub>O  +  4 AuSTg  →  4 Au  +  TgSO<sub>2</sub>H  +  3 TgSH
@@ Line 58: / Line 89: @@
 ==Miscellaneous observations==<!--lame, I know-->
-In recent research, it has found that injection of gold thioglucose in the mouse induces obesity.<ref>{{cite journal | author = Naruta E, Buko V | title = Hypolipidemic effect of pantothenic acid derivatives in mice with hypothalamic obesity induced by aurothioglucose. | journal = Exp Toxicol Pathol | volume = 53 | issue = 5 | pages = 393-8 | year = 2001 | pmid=11817109}}</ref>  Aurothioglucose has an interaction with the [[antimalarial]] medication [[Hydroxychloroquine]].
+In recent research, it was found that injection of gold thioglucose in the mouse induces obesity.<ref>{{cite journal | author = Naruta E, Buko V | title = Hypolipidemic effect of pantothenic acid derivatives in mice with hypothalamic obesity induced by aurothioglucose. | journal = Exp Toxicol Pathol | volume = 53 | issue = 5 | pages = 393–8 | year = 2001 | pmid=11817109 | doi = 10.1078/0940-2993-00205}}</ref>  Aurothioglucose has an interaction with the [[antimalarial]] medication [[hydroxychloroquine]].
 ==See also==
@@ Line 64: / Line 95: @@
 ==References==
-<references/>
+                   {{Reflist|2}}
-==External links==
-<!-- article needs more on its clinical use, cautions, side effects and monitoring. - Is this not covered by link to [[Gold salts]] ? -->
-{{Anti-inflammatory and antirheumatic products}}
-{{SIB}}
-[[Category:Gold compounds]]
+[[Category:Drug]]
 [[Category:IARC Group 3 carcinogens]]
 [[Category:Coordination compounds]]
-[[Category:Immunosuppressive agents]]
+[[Category:Organosulfur compounds]]
-{{WH}}
-{{WS}}