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American Chemical Society, Division of Chemical Information, Education Committee: Computer Searching of Chemical Abstracts: Organic Chemistry (Property) Sample Search.

Organic Chemistry (Substance Property) Sample Search

Search Topic:

Find references dealing with the cardiac toxicity of adriamycin and review articles in English on toxicity of “mycin” antibiotics in general.

Strategy:

  1. Find Registry Numbers for adriamycin.
  2. Key terms
    • adriamycin OR its Registry Numbers
    • toxic? (retrieves toxic, toxicity, toxicol (a CAS abbreviation), toxicology, etc.)
    • cardiac OR heart
  3. Key terms for second part of search
    • ?mycin? (retrieves any term with “mycin” anywhere in the word, such as adriamycin, erythromycin, rapamycin)
    • ?toxic? {retrieves any term with “toxic” anywhere in the word, such as cardiotoxic, cytotoxicity, genotoxic, ecotoxicological, etc.)
  4. Combine the above terms with the (S) operator for greater precision.
  5. Use limiting terms to narrow the search.
    • and review (Adds “review” to search criteria.)
    • english/la (Checks for “English” in the Language field.)

Teaching Points:

Registry File:

CA File:

Search Strategy Table

Search Steps Set Number Number of Documents
file reg
expand adriamycin/cn
S E? L1 1
d L1 ide
fil ca
S L1 L2 1486
S ADRIAMYCIN L3 6486
S L2 OR L3 L4 6732
S TOXIC? L5 263396
S HEART? OR CARDIAC L6 170693
S L4 AND L5 AND L6 L7 658
S L7 AND REVIEW L8 15
D L8 IBIB 1
S ?MYCIN? L9 107563
S ?TOXIC? L10 346606
S L9 (S) L10 (S) L6 L11 622
S L11 NOT L7 L12 108
S L11 AND REVIEW L13 15
S L13 NOT L8 L14 3
S L9 (S) L10 L15 6507
S L15 AND REVIEW AND ENG/LA L16 160
D L16 IBIB 1
LOG Y

Sample Search

Use Registry File to find Registry Numbers for adriamycin

=> file reg

FILE "REGISTRY" ENTERED AT 19:23:21 ON 28 MAY 96 USE IS SUBJECT 
TO THE TERMS OF YOUR CUSTOMER AGREEMENT COPYRIGHT (C) 
1996 American Chemical Society (ACS)

STRUCTURE FILE UPDATES:  25 MAY 96   HIGHEST RN 176705-35-1
DICTIONARY FILE UPDATES: 27 MAY 96   HIGHEST RN 176705-35-4

Use Expand in the chemical name (cn) index to identify the compound

=> expand adriamycin/cn

E1           2     ADRIACIN/CN
E2           1     ADRIADYSIOLIDE/CN
E3           1 --> ADRIAMYCIN/CN
E4           1     ADRIAMYCIN .BETA.-ANOMER/CN
E5           1     ADRIAMYCIN .BETA.-ISOMER/CN
E6           1     ADRIAMYCIN 13-TOSYLHYDRAZONE HYDROCHLORIDE/CN
E7           1     ADRIAMYCIN 14-ACETATE HYDROCHLORIDE/CN
E8           1     ADRIAMYCIN 14-BENZOATE/CN
E9           1     ADRIAMYCIN 14-BENZOATE HYDROCHLORIDE/CN
E10          1     ADRIAMYCIN 14-DECANOATE/CN
E11          1     ADRIAMYCIN 14-NICOTINATE/CN
E12          1     ADRIAMYCIN 14-NICOTINATE 
HYDROCHLORIDE/CN

=> e

E13          1     ADRIAMYCIN 14-OCTANOATE HYDROCHLORIDE/CN
E14          1     ADRIAMYCIN 14-PHENYLACETATE HYDROCHLORIDE/CN
E15          1     ADRIAMYCIN 14-PROPIONATE HYDROCHLORIDE/CN
E16          1     ADRIAMYCIN 14-VALERATE/CN
E17          1     ADRIAMYCIN 14-VALERATE HYDROCHLORIDE/CN
E18          1     ADRIAMYCIN AGLYCONE/CN
E19          1     ADRIAMYCIN DEOXYAGLYCONE SEMIQUINONE/CN
E20          1     ADRIAMYCIN OCTANOYLHYDRAZONE HYDROCHLORIDE/CN
E21          1     ADRIAMYCIN OXIME HYDROCHLORIDE/CN
E22          1     ADRIAMYCIN SEMIQUINONE/CN
E23          1     ADRIAMYCIN, 3-ACETATE/CN
E24          1     ADRIAMYCIN, HYDROCHLORIDE/CN

Search E3 to select our compound.

=> s e3

L1           1 ADRIAMYCIN/CN

Display answer 1 of set L6 in ide format.

=> d L1 ide

L2   ANSWER 1 OF 1  REGISTRY  COPYRIGHT 1996 ACS

RN   25316-40-9  REGISTRY
CN   5,12-Naphthacenedione, 10-[(3-amino-2,3,6-trideoxy-.alpha.-
     L-lyxo-hexopyranosyl)oxy]-7,8,9,10-tetrahydro-6,8,11-
     trihydroxy-8-(hydroxyacetyl)-1-methoxy-, hydrochloride, 
     (8S-cis)- (9CI)  (CA INDEX NAME)
OTHER CA INDEX NAMES:
CN   Adriamycin, hydrochloride (8CI)
OTHER NAMES:
CN   Adriablastina
CN   Adriacin
CN     Adriamycin
CN   Doxorubicin hydrochloride
MF   C27 H29 N O11 . Cl H
CI   COM
LC   STN Files:   ANABSTR, BEILSTEIN*, BIOBUSINESS, 
CA, CAPLUS, CAPREVIEWS, CASREACT, CEN, CHEMCATS,  
CHEMLIST,CBNB, CIN, CJACS, CSCHEM, EMBASE, IFICDB, 
IFIPAT, IFIUDB, IPA, MRCK*, MSDS-OHS, MSDS-SUM, PNI, 
PROMT, RTECS*, TOXLINE, TOXLIT, USAN, USPATFULL 
(*File contains numerically searchable property data)
Other Sources:   EINECS** (**Enter CHEMLIST File for 
up-to-date regulatory information)
DES  *
CRN  (23214-92-8)


                                 OH
                                 .
                                 .
                    Me.          .
                       .       . C.      . NH2
                          . C.     . C .
                            .        .
                            .        .
                            .        .
                            O .    . C
                               . C.
                                 .
                                 .
                                 .
     OMe      O        OH        O
     .        :         .        .
     .        :         .        .
     .        :        .         .
   . C:     . C.     . C :     . C.
  .     :  .     .  .     :   .     .
C        C         C        C        C
:        .         :        .        .
:        .         :        .        .......OH
C.     : C .     . C.     : C.     . C.
   . C:     . C.     . C :     . C.   .
              :        .               .
              :         .              .
              :         .               C....CH2......OH
              O        OH               :
                                        :
                                        :
                                        O



                       @    HCl

6 REFERENCES IN FILE CAPREVIEWS
498 REFERENCES IN FILE CA (1967 TO DATE)
96 REFERENCES TO NON-SPECIFIC DERIVATIVES IN FILE CA
1507 REFERENCES IN FILE CAPLUS (1967 TO DATE)

Use the CA file to identify relevant documents

=> fil ca

Search for L6 (Adriamycin in the Registry File)

=> s L1

L2        1486 L1

Search for the name “adriamycin” in the default fields

=> s adriamycin

L3        6486 ADRIAMYCIN

Search for all articles containing either the Registry Number or the name “adriamycin”

=> s L2 or L3

L4       6732 L2 OR L3

Search for all forms of the word toxic.

=> s toxic?

L5     263396 TOXIC?

Search for all forms of the concept “heart”

=> s heart? or cardiac

       160712 HEART?
        49764 CARDIAC
L6     170693 HEART? OR CARDIAC

Limits the search by combining the chemical compound with “toxic?” and (heart? or cardiac)

=> s L4 and L5 and L6

L7        658 L4 AND L5 AND L6

Continue to limit search to review documents

=> s L7 and review

      1106825 REVIEW
L8         15 L7 AND REVIEW

Display answer 1 of L8 in IBIB Format

=> d L8 ibib 1

L8  ANSWER 1 OF 15  CA  COPYRIGHT 1996 ACS

ACCESSION NUMBER:   122:45417  CA
TITLE:              Utilization of metallothionein inducer in  
                    cancer therapy
AUTHORS:            Naganuma, Akira; Satoh, Masahiko;  
                    Imura, Nobumasa
CORPORATE SOURCE:   S   Sch. Pharm. Sci., Kitsato  
                    Univ.,Tokyo, 108, Japan
SOURCE:             Metallothionein III [Int. Conf.  
                    Metallothionein], 3rd (1993), Meeting Date    
                    1992, 243-53.  Editor(s): Suzuki, Kazuo T.; 
                    Imura,  Nobumasa; Kimura,Masami. Publisher:  
                    Birkhaeuser, Basel, Switz. CODEN: 60TRAK
DOCUMENT TYPE:      Conference; General Review
LANGUAGE:           English

Expand search by using all forms of mycin rather than the Registry Number and the full name.

=> s ?mycin?

L9     107563 ?MYCIN?

Adding to the concept of “toxic” by expanding left via the wild card.

=> s ?toxic?

L10     346606 ?TOXIC?

Note the large number of variations of the word toxic when it is expanded left.

=> expand left toxic

E1           1     BIOTOXIBACILLIN/BI
E2           1     METOXIBUTROPATE/BI
E3      135599 --> TOXIC/BI
E4           1     2GENOTOXIC/BI
E5           1     3CYTOTOXIC/BI
E6           1     4YTOTOXIC/BI
E7           1     6TOXIC/BI
E8           2     6GENOTOXIC/BI
E9          86     ATOXIC/BI
E10          6     ADRENOTOXIC/BI
E11          2     AFLATOXIC/BI
E12          2     AGROTOXIC/BI

Note the large number of variations of the word toxic when it is expanded left.

=> e

E13          1     ALGAETOXIC/BI
E14          1     ALLTOXIC/BI
E15          6     ALLATOTOXIC/BI
E16          9     ALLOCYTOTOXIC/BI
E17          1     ALLOLYMPHOCYTOTOXIC/BI
E18          1     ALVEOLOTOXIC/BI
E19          2     AMATOXIC/BI
E20          1     AMBRYOTOXIC/BI
E21          1     ANAGOTOXIC/BI
E22         32     ANAPHYLATOXIC/BI
E23          1     ANAPHYLOTOXIC/BI
E24         25     ANGIOTOXIC/BI

Now the ?mycin?, heart? or cardiac?, and ?toxic? terms are ‘and’ed together. Note this search is similar to L7 but uses broader search terms (ie ?toxic? rather than toxic?) but narrowed search stategy (use of S). Overall, it provides fewer sources.

=> s L9 (s) L10 (s) L6

L11        622 L9 (S) L10 (S) L6

Displays which new documents were found with L11 that were not found in L7.

=> s L11 not L7

L12        108 L11 NOT L7

Limits search by locating review documents

=> s L11 and review

       1106825 REVIEW
L13         15 L11 AND REVIEW

Selects which review documents were found with L13 and not with L8

=> s L13 not L8

L14          3 L13 NOT L8

This is the same as L11 except the heart? or cardiac limitation has been removed.

=> s L9 (s) L10

L15       6507 L9 (S) L10

This limits L15 by restricting to review (‘review’) and english (eng) language (/la)

=> s L15 and review and eng/la

        106825 REVIEW
       7859140 ENG/LA/
L16        160 L15 AND REVIEW AND ENG/LA

Displays (d) answer 1 (1) of search L16 (L16) in IBIB form

=> d L16 ibib 1

L16  ANSWER 1 OF 160  CA  COPYRIGHT 1996 ACS

ACCESSION NUMBER:  124:277534  CA
TITLE:             Tobramicin: clinical pharmacology and 
                   chemotherapy
AUTHOR:            Periti, P.
CORPORATE SOURCE:  Dipartimento di Farmacologia 
                   Precliniica e Clinica, Universita degli Studi, 
                   Firenze, Florence, 50134, Italy
SOURCE:            J. Chemother. (Florence) (1996), 8(Suppl. 1), 
                   3-30 CODEN: JCHEEU;  ISSN: 1120-009X
DOCUMENT TYPE:     Journal; General Review
LANGUAGE:          English

Log off in one step

=> log y
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